Tag: M.W=200-300

Recommanded Product: 6-Bromo-8-methylquinoline. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 6-Bromo-8-methylquinoline, is researched, Molecular C10H8BrN, CAS is 178396-31-1, about Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes via C(sp3)-H bond activation of 8-methylquinoline. Author is Tan, Heng; Khan, Ruhima; Xu, Dandan; Zhou, Yongyun; Zhang, Xuexin; Shi, Guangrui; Fan, Baomin.

The first ring-opening addition of a benzylic C(sp3)-H bond to azabenzonorbornadienes is demonstrated. The reaction proceeded under the catalytic system of [Cp*CoI2(CO)], AgSbF6 and Fe(OAc)2 in PhOMe. The methodol. showed a good substrate scope with up to 96% yield. The relative configuration of the product was determined as cis-configuration by X-ray crystallog.

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Wipf, Peter; Wang, Xiaodong published an article about the compound: (R)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride( cas:323196-43-6,SMILESS:O=C1N(C)C(C)(C)N[C@@H]1CC2=CC=CC=C2.[H]Cl ).COA of Formula: C13H19ClN2O. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:323196-43-6) through the article.

Catalytic asym. Diels-Alder reactions with an amino diene, (E)-H(CH:CH)2NHCO2CH2Ph, and a desymmetrized fumarate, N-[3-(methoxycarbonyl)-2-propenoyl]-2-oxazolidinone, were used for efficient access to dihydroxylated cis- and trans-aminocyclohexane β-amino acids.

Compound(323196-43-6)COA of Formula: C13H19ClN2O received a lot of attention, and I have introduced some compounds in other articles, similar to this compound((R)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride), if you are interested, you can check out my other related articles.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some derivatives of 6-bromo-8-methylquinoline and 6-chloro-8-methylquinoline》. Authors are Irving, Thurman A.; Greene, Joseph L. Jr.; Peterson, Joe G.; Capps, Julius D..The article about the compound:6-Bromo-8-methylquinolinecas:178396-31-1,SMILESS:CC1=CC(Br)=CC2=C1N=CC=C2).Recommanded Product: 178396-31-1. Through the article, more information about this compound (cas:178396-31-1) is conveyed.

cf. C.A. 44, 9965f. 6-Chloro-8-methylquinoline picrate m. 223-4°. 2-Acetamido-5-bromo-4-nitrotoluene (I), m. 153-4°; the Cl analog m. 142-3° [Reverdin and Crepieux, Ber. 33, 2505(1900), gave 262°]. Skraup ring closure of 8 g. I gives 1.9 g. 6-bromo-8-methyl-5-nitroquinoline (II), m. 117-18°; 6-Cl analog (III), m. 99-100°, 9.3%. By the previous method, II yields 76% crude 6-bromo-1,8-dimethyl-2(1H)-quinolone (IV), m. 76-81°, which with POCl3-PCl5 gives 76% 6-bromo-2-chloro-8-methylquinoline (V), m. 120-1°; 6-Cl analog of IV, m. 64-5°, 75%; 6-Cl analog (VI) of V, m. 121-2°, 78%. V (2 g.) in 25% (by volume) H2SO4, heated 2 h. at 175-80° (autoclave), gives 84% 6-bromo-2-hydroxy-8-methylquinoline, m. 280-1°; 6-Cl analog (9.1 g. from 10 g. VI), m. 265-6°. I (25 g.) and 20 mL. Me2SO4, heated 1 h. at 150-70° and 1.5 h. at 145° and oxidized with 30% H2O2 at 55-65°, give 65% 6-bromo-1,8-dimethyl-5-nitroquinolone (VII), m. 158-9°; crude Cl analog, m. 121-2° (decomposition). VII yields 69% 2,6-dibromo-8-methyl-5-nitro-2(1H)-quinoline, m. 160-1°; 2,6-di-Cl compound, m. 137-8°, 73%. 6-Bromo-2-hydroxy-8-methyl-5-nitroquinoline, m. 311-12°, 87%; 6-Cl analog, m. 271-2°. Reduction in Me2CO or absolute EtOH over Raney Ni gives the following: 5-amino-6-bromo-8-methylquinoline, m. 116-17°, 73% (Ac derivative, m. 235-6°, 81%; Bz derivative, m. 210-11°, 69%); 6-Cl analog, m. 113-14°, 92% (Ac derivative, m. 225-6°, 82%; Bz derivative, m. 193-4°, 79%); 5-amino-2-chloro-6-bromo-8-methylquinoline, m. 127-8° (6 g. from 10 g. NO2 compound) (Ac derivative, m. 272-3°, 84%; Bz derivative, m. 252-3°, 60%); 5-amino-2,6-dichloro-8-methylquinoline, m. 132-3°, 96% (Ac derivative, m. 265-6°, 84%; Bz derivative, m. 253-4°, 65%); 5-amino-2-hydroxy-6-bromo-8-methylquinoline, m. 238-9°, 89% [Ac derivative, m. 318-19° (decomposition); Bz derivative, m. 297-8°, 75%]; 5-amino-2-hydroxy-6-chloro-8-methylquinoline (Ac derivative, m. above 340°, 54%; Bz derivative, m. 331-2°, 93%). By the Bart reaction (cf. Capps and Hamilton, C.A. 32, 8421.4) were prepared: 6-bromo-8-methyl-5-quinoline arsonic acid, m. 244-5° (decomposition), 10.5%; 6-Cl analog, m. 255-6°, 17%; 2-chloro-6-bromo analog, m. above 330°, 7.7%; 2,6-di-Cl compound, m. 302-3°, 6.7%; 2-hydroxy-6-bromo analog, m. above 330°, 8.8%; 2-hydroxy-6-chloro analog, m. 325-6°, 6.5%.

From this literature《Some derivatives of 6-bromo-8-methylquinoline and 6-chloro-8-methylquinoline》,we know some information about this compound(178396-31-1)Recommanded Product: 178396-31-1, but this is not all information, there are many literatures related to this compound(178396-31-1).

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 6-Bromo-8-methylquinoline( cas:178396-31-1 ) is researched.Recommanded Product: 6-Bromo-8-methylquinoline.Kumar, Rohit; Kumar, Rakesh; Parmar, Diksha; Gupta, Shiv Shankar; Sharma, Upendra published the article 《Ru(II)/Rh(III)-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Activation: Selective Linear Alkylation of 8-Methylquinolines and Ketoximes with Olefins》 about this compound( cas:178396-31-1 ) in Journal of Organic Chemistry. Keywords: alkylquinoline alkylsantonin oxime regioselective preparation; ruthenium rhodium catalyst regioselective alkylation methylquinoline acrylate styrene alkene; regioselective alkylation methylquinoline santonin oxime ether alkene ruthenium catalyst; rhodium catalyst regioselective alkylation methylquinoline santonin oxime ether alkene; mechanism kinetic isotope effect regioselective alkylation methylquinoline acrylate. Let’s learn more about this compound (cas:178396-31-1).

In the presence of either [RuCl2(p-cymene)]2 or [Cp*RhCl2]2 and AgSbF6, 8-methylquinolines underwent regioselective alkylation with acrylates, styrenes, and other alkenes mediated by pivalic acid in hexafluoroisopropanol to yield 8-alkylquinolines with linear alkyl substituents. The mechanism of the reaction was studied using deuterium labeling, kinetic isotope effect, and competition studies; the reaction may proceed through a five-membered metallacycle intermediate. Under similar conditions, an O-methyloxime derivative of (-)-santonin underwent regioselective alkylation with Et acrylate and acrylonitrile.

If you want to learn more about this compound(6-Bromo-8-methylquinoline)Recommanded Product: 6-Bromo-8-methylquinoline, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(178396-31-1).

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Barsu, Nagaraju; Rahman, Atiur Md.; Sen, Malay; Sundararaju, Basker published the article 《Cp*CoIII-Catalyzed C(sp3)-H Bond Amidation of 8-Methylquinoline》. Keywords: quinolinylmethylamide preparation; methylquinoline oxazolone amidation cobalt catalyst; amidation; cobalt; quinoline; sp3 C−H activation.They researched the compound: 6-Bromo-8-methylquinoline( cas:178396-31-1 ).Quality Control of 6-Bromo-8-methylquinoline. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:178396-31-1) here.

An efficient and external oxidant-free, Cp*CoIII-catalyzed C(sp3)-H bond amidation of 8-methylquinoline, using oxazolone as an efficient amidating agent, is reported for the first time under mild conditions. The reaction is selective and tolerates a variety of functional groups. Based on previous reports and exptl. results, the deprotonation pathway proceeds through an external base-assisted concerted metalation and deprotonation process.

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Yu, Songjie; Tang, Guodong; Li, Yingzi; Zhou, Xukai; Lan, Yu; Li, Xingwei published an article about the compound: 6-Bromo-8-methylquinoline( cas:178396-31-1,SMILESS:CC1=CC(Br)=CC2=C1N=CC=C2 ).Product Details of 178396-31-1. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:178396-31-1) through the article.

Previous direct C-H nitrogenation suffered from simple amidation/amination with limited atom-economy and is mostly limited to C(sp2)-H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp2)-H and C(sp3)-H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl, e. g., I. A tridendate rhodium(III) complex has been isolated as the resting state of the catalyst, and DFT studies established the intermediacy of a nitrene species.

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Related Products of 10233-13-3, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 10233-13-3, Name is Isopropyl dodecanoate, SMILES is CCCCCCCCCCCC(OC(C)C)=O, belongs to esters-buliding-blocks compound. In a article, author is Kim, Kun-Pyo, introduce new discover of the category.

Borage oil [BO: 40.9% linoleic acid (LNA) and 24.0% gamma-linolenic acid (GLA)] reverses disrupted epidermal lipid barrier in essential fatty acid deficiency (EFAD). We determined the effects of BO on lamellar body (LB) content and LNA and GLA incorporation into epidermal ceramide 1 (CER1) and epidermal ceramide 2 (CER2), major barrier lipids. EFAD was induced in guinea pigs by a diet of 6% hydrogenated coconut oil (HCO) for 10 weeks (group HCO) or 8 weeks followed by 6% BO for 2 weeks (group HCO + BO). LB content and LNA and GLA incorporation into CER1 were higher in group HCO + BO than in group HCO. Small but significant levels of LNA, GLA, and their C20-metabolized fatty acids [dihomo-gamma-linolenic acid (DGLA) and arachidonic acid (ARA)] were incorporated into CER2, where ARA was detected at a level lower than LNA, but DGLA incorporation exceeded that for GLA in group HCO + BO. Dietary BO enhanced LB content and differential incorporation of GLA into CER1 and DGLA into CER2.

Related Products of 10233-13-3, Because enzymes can increase reaction rates by enormous factors and tend to be very specific, typically producing only a single product in quantitative yield, they are the focus of active research.you can also check out more blogs about 10233-13-3.

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Ester – Wikipedia,
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Related Products of 54535-22-7, A common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

j00330J A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHU, Cathy; DOKOU, Eleni; HASELTINE, Eric L.; MOSKOWITZ, Samuel; OVERHOFF, Kirk A.; ROBERTSON, Sarah; WALTZ, David; (204 pag.)WO2019/10092; (2019); A1;,
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Reference of 148547-19-7,Some common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24. 88-MMOL), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 * 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methyl acrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o-tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 ML, 1M). The product is extracted with dichloromethane (2 * 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M+1 207. The structure is confirmed by : L H NMR spectroscopy.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63184; (2004); A1;,
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Electric Literature of 17449-48-8,Some common heterocyclic compound, 17449-48-8, name is Dimethyl 5-fluoroisophthalate, molecular formula is C10H9FO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Concentrated [HC1] (30 ml) was added to a cooled [(-5C)] suspension of dimethyl 5-amino isophthalate (20 g, 95.6 mmol) in water (75 ml), followed by portionwise addition of [NAN02] (7.5 g, 109 mmol). The reaction mixture was then stirred for 15 min. , after which [HBF4 (18] ml, 100 mmol, 48% aqueous solution) was added. The resulting mixture was stirred at [0C] for 30 min. and the precipitate formed was collected by filtration and washed with cold methanol (60 ml) and ether (60 ml). The residue was then decomposed by heating in an oil bath [(~110C).] The cooled mixture was then diluted with ether, concentrated onto silica gel and purified by flash chromatography with 5% ethyl acetate hexane as eluant giving 9.0 g (44%) of product as a white fluffy [SOLID. LH NE (CDC13), 6] [(PPM)] : 8.57 (s, 1H), 7.95 (d, 2H), 3.97 (s, 6H). A suspension of 5-fluoro-isophthalic acid dimethyl ester (1.7 g, 8. 0 mmol) in methanol (41 ml) was treated with 1.0 N sodium hydroxide (7.2 ml, 7.2 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1.0 N [HC1] to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 1.3 g (83%) of 5-fluoro-isophthalic acid monomethyl ester was isolated as a white [SOLID. LH] NMR (DMSO), [5] (ppm): 8.31 (t, 1H), 7.96 (m, 2H), 3.91 (s, 3H). Triethylamine (2.2 ml, 16.0 mmol) and isobutyl [CHLOROFORMATE] (1.0 ml, 8. 0 mmol) were added to an ice-cooled solution [OF 5-FLUORO-ISOPHTHALIC] acid monomethyl ester (1.3 g, 6.7 mmol) in dichloromethane (20 ml) and then warmed to room temperature. After stirring for 2 h, the reaction mixture was filtered and concentrated. The residue was re-dissolved tetrahydrofuran (10 ml) and then sodium borohydride [(1.] 1 g, 29.02 mmol) in water (3ml) was added drop-wise. After 1 h, the reaction was quenched with methanol and then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Flash column chromatography on silica gel using 30% ethyl acetate in hexanes afforded 667 mg (54%) of 3-fluoro-5-hydroxymethyl-benzoic acid methyl ester as a colorless [OIL. 1H] NMR [(CDC13),] [8] (ppm): 7.82 (s, 1H), 7.63 (d, 1H), 7.32 (d, 1H), 4.76 (s, 2H), 3.93 (s, 3H). Ethanol (2 ml) was added to round bottom flask containing 3-fluoro-5-hydroxymethyl- benzoic acid methyl ester (667 mg, 3.6 mmol) and palladium (10 wt. % on activated carbon, 300 mg) under argon. The flask was evacuated using a water aspirator and then filled with hydrogen from a balloon. After stirring for 2 h, the palladium on carbon was removed by filtration through celite. The filtrate was then concentrated to afford 520 mg (87%) of 3-fluoro-5-methyl-benzoic acid methyl [ESTER. LH] NMR [(CDC13),] 8 (ppm): 7.65 (s, 1H), 7.51 (d, 1H), 7.08 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H). 0.5 N Lithium hydroxide (7.4 ml, 3.7 mmol) was added to a solution 3-fluoro-5-methyl- benzoic acid methyl ester (520 mg, 3.1 mmol) in tetrahydrofuran (7.4 ml). The reaction was stirred at [75 C] for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 10% [HC1] (aq. ). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 469 mg (98%) [OF 3-FLUORO-5-METHYL-BENZOIC] acid as a white solid. 1H NMR (DMSO), d (ppm): 7.62 (s, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 2.38 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 5-fluoroisophthalate, its application will become more common.

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
Ester – Wikipedia,
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