Month: May 2021

Synthetic Route of 22223-49-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22223-49-0 name is Methyl 2-amino-3-methylbenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: CuCl (1.50 mg, 0.0150 mmol), DPEPhos (8.10 mg, 0.0150 mmol) and KOt-Bu (1.70 mg,0.0150 mmol) were added to a 8 mL vial charged with a magnetic bar. The vial was sealedwith a cap (phenolic open top cap with gray PTFE/silicone) and purged by N2 gas for 5 min.Toluene (0.8 mL) and methyl 2-aminobenzoate (1a) (46.6 L, 0.360 mmol) were added to themixture, which was allowed for 10 min. And then a solution of phenyl vinyl sulfone (2) (50.5mg, 0.300 mmol) in toluene (0.7 mL) was added to the reaction solution. After stirring atroom temperature for 5 h, THF (5 mL) was added and the reaction was allowed to cool to 0C (ice bath). After addition of KOt-Bu (101 mg, 0.900 mmol), the resulting solution wasallowed to stir for further 1 h at 0 C. After that time, the reaction was quenched with asaturated aqueous solution of NH4Cl (1 mL) and NaHCO3 (2 mL) and washed with EtOAc (7x 3 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated invacuo. The crude product was purified by silica gel column chromatography (CH2Cl2/EtOAc,8:1) to afford the desired product 4a (76.8 mg, 0.267 mmol, 89% yield) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Kang, Seongil; Yoon, Hongju; Lee, Yunmi; Chemistry Letters; vol. 45; 12; (2016); p. 1356 – 1358;,
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Related Products of 120-61-6,Some common heterocyclic compound, 120-61-6, name is Dimethyl terephthalate, molecular formula is C10H10O4, 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 solution of 4.01 g of dimethyl terephthalate in methanol and 42 g of a methanol solution of dimethyl terephthalate was prepared.0.4003 g of the activated-passivated nickel-containing catalyst and 0.8005 g of the copper-based catalyst were added and hydrogenation reaction was carried out at 200 C. under a hydrogen pressure of 4 MPa and stirring at 700 r/min for 4 h. The temperature was then raised to 240C, the hydrogen pressure was adjusted to 8 MPa, and the reaction was carried out for 4 hours while stirring at 700 r/min. After the reaction was cooled down to room temperature overnight, the catalyst was separated by centrifugation, filtration, and the solution was distilled to obtain 1,4-cyclohexanedimethanol product after purification. The yield was 92%.

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

Reference:
Patent; Shandong Yuhuang Chemical Co., Ltd.; Yuan Benfu; Pang Fei; Guo Chunping; Xu Longkun; Wang Rongguang; Wang Hui; Wang Zhongya; Hou Hongxia; Wang Jianwei; Wang Shengwei; (6 pag.)CN107805183; (2018); A;,
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These common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, 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. Formula: C6H8O2

Compound A (ethyl 2-butynoate, 1.12 g, 10 mmol) was dissolved in tetrahydrofuran.Add N,O-dimethylhydroxylamine hydrochloride (1.94 g, 20 mmol),Cool to -40 C,Isopropylmagnesium chloride (2M/L, 15 mL, 30 mmol) was added and reacted for 1 h.The reaction was completed, quenched with water, ethyl acetate (200 mL¡Á3), and brine (100 mL¡Á6)Concentrated under reduced pressure and purified by silica gel column chromatographyCompound B (colorless oil, 1.15 g, 91%).

The synthetic route of Ethyl 2-butynoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou University; Tu Yongqiang; Zhang Qing; (20 pag.)CN109666030; (2019); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 59833-69-1 as follows. Product Details of 59833-69-1

General procedure: To a stirred solution of 35c (781 mg, 3.9 mmol) and pyridine (0.95 mL, 11.7 mmol) in CH2Cl2 (10 mL) was added a solution of 34a (1.3 g, 3.9 mmol) in CH2Cl2 (10 mL). After stirring overnight at room temperature, the reaction mixture was quenched with water and extracted with EtOAc (¡Á2). The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (1.3 g, 63% in 2 steps) as a pale yellow amorphous powder.

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Naganawa, Atsushi; Kinoshita, Atsushi; Shimabukuro, Atsushi; Nishiyama, Toshihiko; Ogawa, Seiji; Matsunaga, Yoko; Tsukamoto, Kohki; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Oumi, Rie; Odagaki, Yoshihiko; Katagi, Jun; Yano, Koji; Tani, Kousuke; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 22; (2011); p. 6935 – 6948;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4891-38-7, COA of Formula: C10H8O2

General procedure: To the mixture of terminal alkyne (1mmol), water (2.0 equiv), and acetic acid (2 mL), silver tetrafluoroborate (5 mol%) was added. The mixture was stirred at 110C for 10 h. Water (10 mL) was added and the solution was extracted with ethyl acetate (3¡Á8 mL), the combined extract was dried with anhydrous MgSO4. The solvent was removed and the crude product was separated by column chromatography to give the pure sample.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl Phenylpropiolate, and friends who are interested can also refer to it.

Reference:
Article; Chen, Zheng-Wang; Ye, Dong-Nai; Qian, Yi-Ping; Ye, Min; Liu, Liang-Xian; Tetrahedron; vol. 69; 30; (2013); p. 6116 – 6120;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 105-53-3, name is Diethyl malonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 105-53-3, Application In Synthesis of Diethyl malonate

EXAMPLE 1 Preparation of ethyl 2-ethoxycarbonyl-4-methylvalerate Diethyl malonate (20 g; 124.8 mmoles) was added to a mixture of metallic sodium (2.87 g; 124.8 mmoles) dissolved in absolute ethanol (60 ml) at 50 C. After 1 hour at room temperature isobutyl bromide 97% (16.78 g; 118.8 mmoles) was added dropwise. After 2.5 hours at reflux temperature, the reaction mixture was kept at room temperature overnight. After adding hydrochloric acid 1N up to pH 4-5, ethanol was evaporated and the residue was extracted with ethyl ether. After drying and evaporating the solvent at reduced pressure, the crude oil was purified by distillation at 78 C./2.5 mmHg after the removal of the exceeding diethyl malonate at 65 C./7 mmHg. Ethyl 2-ethoxycarbonyl-4-methylvalerate (14.4 g; 56% yield) was obtained as a colorless oil. 1 H-NMR (200 MHz, CDCl3): delta (ppm): 0.87 (d, 6H); 1.21 (t, 6H); 1.52 (m, 1H); 1.75 (t, 2H); 3.47 (t, 1H); 4.15 (q, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl malonate, and friends who are interested can also refer to it.

Reference:
Patent; Zambon Group S.p.A.; US5739123; (1998); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 36692-49-6, These common heterocyclic compound, 36692-49-6, name is Methyl 3,4-diaminobenzoate, 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.

To a solution of 3,4-diamino-benzoic acid methyl ester (5.00 g, 30.1 mmol) and THF (40 ml_), was added carbonyl diimidazole (7.32 g, 45.1 mmol) at 0 0C. The mixture stirred for 16 h, and allowed to warm to 23 0C. A solution of 1 M aq. HCI (50 ml_) was added at 0 0C, followed by water (70 ml_) and the mixture was stirred for 1 h. The resulting precipitate was filtered and dried under reduced pressure for 18 h to yield the titled compound, which was used in the next step without further purification (5.45 g, 94 %). MS (ESI/CI): mass calcd. for C9H8N2O3, 192.1 ; m/z found, 193.1 [M+H]+. 1H NMR (400 MHz, CDCI3): 11.01 (s, 1 H), 10.84 (s, 1 H), 7.63 (dd, J = 8.2, 1.6 Hz, 1 H), 7.47 (s, 1 H), 7.02 (d, J = 8.2 Hz, 1 H), 3.82 (s, 3H).

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/134750; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 122-63-4, name is Benzyl propionate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 122-63-4, Product Details of 122-63-4

To a solution of benzyl propionate (2.46 g, 15.0 mmol) in anhydrous THF (30 mL) at -78 C was added dropwise LDA (2.0 M, 7.5 mL). The mixture was stirred for 30 min, and then tert-butyl 4-oxopiperidine-l-carboxylate (3.0 g, 15.0 mmol) in anhydrous THF (20 mL) was added. This mixture was stirred at -78 C for 1 h, then quenched with sat aqueous H4CI (30 mL) and extracted with EtOAc (50 mLx3). The combined organic extracts were washed with brine and dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column (pet ether: EtOAc 3 : 1) to give the desired product as a white solid (2.5 g). Yield 46 % (ESI 264.2 (M+H-100) +).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; LAZULI, INC.; HARRISON, Bryce, Alden; BURSAVICH, Matthew, Gregory; GERASYUTO, Aleksey, Lgorevich; HAHN, Kristopher, Neil; KONZE, Kyle, David; LIN, Fu-Yang; LIPPA, Blaise, Scott; LUGOVSKOY, Alexey, Alexandrovich; ROGERS, Bruce, Nelsen; SVENSSON, Mats, Ake; TROAST, Dawn, Marie; (0 pag.)WO2018/160522; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 135484-83-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00404] Step A: Methyl 2-amino-4-bromobenzoate was prepared from the corresponding acid by Fischer esterification. A mixture of methyl 2-amino-4- bromobenzoate (1.1 g, 4.8 mmol) and ethyl carbonocyanidate (0.95 g, 9.66 mmol) in HOAc (4 mL) was treated with a sl2 N HCl (0.4 mL) and the resulting mixture was stirred at 700C for 3 h. After cooling to rt, water was added followed by addition of aq sodium hydrogen carbonate to pH ~5. The precipitated solid was filtered and washed thoroughly with water and diethyl ether to afford ethyl 7-bromo-4-oxo-3,4- dihydroquinazoline-2-carboxylate (825 mg, 58%). 1H NMR (300 MHz, DMSO-d6) delta 12.82 (s, IH), 8.06-8.09 (m, 2H), 7.81 (d, J= 8.4 Hz, IH), 4.38 (q, J= 7.0 Hz, 2H), 1.35 (t, J= 7.0 Hz, 3H); LC-MS (ESI) m/z 296 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
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Electric Literature of 2435-36-1,Some common heterocyclic compound, 2435-36-1, name is Dimethyl cyclopentane-1,3-dicarboxylate, molecular formula is C9H14O4, 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.

Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate. n-Butyllithium (2.5 M in hexane, 419.0 mL, 1048 mmol) was added slowly to a solution of diisopropylamine (152 mL, 1090 mmol) and anhydrous THF (1000 mL) at -78 C. (dry ice/acetone) under N2. Next, the reaction was stirred for 0.5 hours at 0 C. before cooling to -78 C. DMPU (404 mL, 3350 mmol) was added via an addition funnel. Then a solution of dimethyl cyclopentane-1,3-dicarboxylate (78.0 g, 419 mmol) and anhydrous THF (300 mL) was added slowly via an addition funnel. The reaction was warmed to 0 C. and stirred for 30 minutes, then cooled to -78 C. and treated with a solution of 1-bromo-2-chloroethane (59.0 mL, 712 mmol) and anhydrous THF (200 mL). The reaction was allowed to warm slowly to room-temperature and was stirred for 12 hours at room-temperature. The reaction was quenched with saturated aqueous ammonium chloride (400 mL). The reaction was diluted with ethyl acetate (500 mL), the organic layer separated, and the aqueous layer was further extracted with ethyl acetate (2¡Á500 mL). The combined organic extracts were washed with brine (2¡Á300 mL), dried over anhydrous MgSO4, filtered, and concentrated to dryness. The residue was filtered through a pad of silica gel and washed with ethyl acetate (2000 mL). The filtrate was concentrated to dryness and the residue was purified by flash column chromatography (petroleum ether/ethyl acetate, 30:1 to 20:1, gradient elution) to provide the title compound (48.5 g, 54%) as white solid. 1H NMR (400 MHz, CDCl3): delta 3.69 (s, 6H), 2.08-1.99 (m, 4H), 1.91 (s, 2H), 1.73-1.63 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl cyclopentane-1,3-dicarboxylate, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Koudriakova, Tatiana; Kreutter, Kevin D.; Leonard, Kristi; Rizzolio, Michele C.; Smith, Russell C.; Tichenor, Mark S.; Wang, Aihua; (40 pag.)US2018/170931; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics