Category: 18595-14-7

Related Products of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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.

Step 1. Synthesis of methyl 4-[(4-fluorobenzoyl)amino]-3-methylbenzoate Following standard procedure, 4-fluorobenzoic acid (0.510 g, 3.63 mmol), methyl 4-amino-3-methylbenzoate (0.500 g, 3.03 mmol), EDCI · HCl (1.16 g, 6.06 mmol), DMAP (0.930 g, 7.57 mmol) and CH2Cl2 (7.0 mL) were used to carry out the reaction. After the reaction mixture was stirred at room temperature for 16 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-40% ethyl acetate in n-hexane) to give methyl 4-[(4-fluorobenzoyl)amino]-3-methylbenzoate (0.380 g, 44%). 1H NMR (CDCl3, 400 MHz) delta 8.23 (d, 1H), 7.96-7.88 (m, 4H), 7.75 (br s, 1H), 7.20 (td, 2H), 3.91 (s, 3H), 2.39 (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 Methyl 4-amino-3-methylbenzoate, its application will become more common.

Reference:
Patent; National Health Research Institutes; Ueng, Shau-Hua; Yeh, Shiu-Hwa; Lin, Shu-Yu; Shih, Chuan; (329 pag.)US2017/253569; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, 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 18595-14-7, Computed Properties of C9H11NO2

An autoclave was charged with a mixture of methyl 4-amino-3-methylbenzoate (10.0 g, 60.5 mmol, Cas No18595-14-7), rhodium 5% on charcoal (3.74 g, 50% wet), acitic acid (5.2 ml)and ethanol (100 ml) and pressurized with hydrogen (12 bar). The mixture was stirred at 80C for 22 h. For work-up, the catalyst was filtrate d off, washed with ethanol and the filtratewas concentrated under reduced pressure. The residue was dissolved in dichloromethane(250 ml) and hydrochloric acid (30 ml, 120 mmol, 4 M in dioxane) was added. The mixturewas concentrated und reduced pressure and the residue was codestilled with toluene (2x) togive the crude product as a mixture of isomers which was used without further purification.

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 4-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Ester – Wikipedia,
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Application of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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.

General procedure: Methyl 4-amino-3-methylbenzoate (6) (10.00g, 60.58mmol) was acylated with alkyl acyl chloride (90.87mmol) and triethylamine (16.79mL, 121.16mmol) in DCM at 0C. The resulting amide was reacted with fuming nitric acid in sulfuric acid (60%) at-20C. The resulting nitro-compound was reduced with hydrogen (5bar) and Raney Ni (0.79g, 13.34mmol) in methanol at 100C. The resulting amino compound was dissolved in glacial acetic acid and heated under reflux for 1h. After evaporation of the acetic acid, water was added and the pH was adjusted to 9 by addition of concentrated ammonia. This solution was extracted with ethyl acetate (3×100mL). The combined organic layers were washed with aqueous NaHCO3 solution and dried over MgSO4. After filtration, the solvent was removed under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-methylbenzoate, its application will become more common.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
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Ester – an overview | ScienceDirect Topics

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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 18595-14-7

To a stirred and cooled (0 C) slurry of commercially available methyl 4-amino-3-methylbenzoate (2 g, 12.12 mmol) in 6 N HCl (12 mL) was added NaNO2 (0.92 g, 13.33 mmol) in water (2 mL) drop wise maintaining a temperature of <15 C during the addition. The mixture was stirred an additional 1.5 h affording a light yellow, homogeneous solution. To the mixture was carefully added 4.58 g (24.24 mmol) of anhydrous SnCl2. The temperature during the addition was kept <10 C. The mixture was stirred at 0 C for 1 h. The precipitated solid was collected by filtration, dried under vacuum to afford methyl 4-hydrazinyl-3-methylbenzoate hydrochloride 4 (1.75 g 81%) as a brown solid: mp 224-226 C; 1H NMR (CDCl3, 500 MHz) delta ppm 2.22 (s, 3H), 3.80 (s, 3H), 6.99 (d, J = 8.5 Hz, 1H), 7.70 (s, 1H), 7.77 (d, J = 8.5 Hz, 1H); MS (ESI): m/z calcd for C9H12N2O2 ([M+H]+) 181.0932; found 181.0911 ([M+H]+). The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings. Reference:
Article; Chiruta, Chandramouli; Zhao, Yanrong; Tang, Fangling; Wang, Tao; Schubert, David; Bioorganic and Medicinal Chemistry; vol. 21; 10; (2013); p. 2733 – 2741;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 18595-14-7

A solution of sodium nitrite (4.60 g, 66.6 mmol, 1.10 equiv) in water (50 mL) was added slowly to a pre-cooled (-10 C) mixture of methyl 4-amino-3-methylbenzoate (12-1, 10.0 g, 60.5 mmol, 1 equiv) and concentrated aqueous hydrochloric acid solution (12 M, 15.1 mL, 182 mmol, 3.00 equiv) in water (75 mL) at a rate that kept the reaction mixture temperature below 0 C. Following the addition, the reaction mixture was stirred at -5 C for 30 min, then filtered. A solution of sodium tetrafluoroborate (20.0 g, 182 mmol, 3.00 equiv) in water (100 mL) was immediately added to the cold filtrate. The precipitate was filtered and washed with ice-cold water (70 mL). The remaining solid was air-dried to give 4-(methoxycarbonyl)-2-methylbenzenediazonium tetrafluoroborate as a white solid. A suspension of this product (16.0 g, 60.6 mmol, 1 equiv), potassium acetate (14.9 g, 152 mmol, 2.50 equiv) and 18- crown-6 (1.60 g, 6.06 mmol, 0.100 equiv) in chloroform (300 mL) was stirred at 23 C for 5 h. The reaction mixture was filtered and concentrated. The residue was partitioned between water and EtOAc (300 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated to give methyl lH-indazole-5-carboxylate (12-2) as a light orange solid. LRMS m/z (M+Eta) 177.1 found, 177.1 required.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/86255; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 18595-14-7, 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. 18595-14-7 name is Methyl 4-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.

Under a nitrogen atmosphere, to a 100-mL four-necked flask were added 5-methylmenthyl carboxylic acid (rac-11a) (600 mg, 3.03 mmol) obtained in Synthesis Example 7, 8, 9, or 19, thionyl chloride (0.33 mL, 1.50 eq.), and a catalytic amount of DMF, followed by stirring at room temperature for 3 hours. The solution in the system was distilled off under reduced pressure, and toluene (2 mL) was added thereto. The inside of the system was cooled to 10 C. or lower in an ice bath, and 3-methyl-4-aminobenzoic acid methyl ester (1.50 g, 3.0 eq.) was added slowly thereto. After two and a half hours, completion of the reaction was confirmed by GC-MS, and a post-treatment was performed. The reaction solution was transferred to a separating funnel, and tap water and chloroform were added thereto to effect washing. The oil layer was washed twice with dilute hydrochloric acid, and further washed once with a saturated saline solution, and then dried with anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and then isolation and purification were performed by column chromatography (heptane/ethyl acetate=4/1), whereby an amorphous solid was obtained (306 mg, yield: 29%). HRMS: mass: 345.2304 actual measurement value: 345.2298 1H-NMR (500 MHz, CDCl3): delta0.85-0.98 (m, 12H), 1.20-1.33 (m, 3H), 1.45-1.65 (m, 4H), 1.82 (quid, 1H, J=6.6, 2.1 Hz), 2.29-2.40 (m, 4H), 7.05 (br, 1H), 7.86-7.90 (m, 2H), 8.14 (d, 1H, J=8.2 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; ITOH, Hisanori; HORI, Yoji; OTSUKA, Masashi; MATSUMOTO, Takaji; SATO, Tomoharu; (50 pag.)US2018/57447; (2018); A1;,
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18595-14-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-amino-3-methyl-benzoate (12.17 g, 73.70 mmol) in DCM (135 mL) was added 1-pyridin-1-ium-1-yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (30.14 g, 81.00 mmol). The reaction mixture was stirred for 1.5h, then 1-pyridin-1-ium-1- yliodanuidylpyridin-1-ium (Boron Tetrafluoride Ion) (2.740 g, 7.367 mmol) was added and the mixture was stirred for another 2h, then quenched with aqueous saturated NaHCO3 (100 mL).The layers were separated. The aqueous layer was extracted with DCM (2 x 100 mL). The combined organic extracts were washed with aqueous 1M Na2S2O3 (100 mL) and dried over Na2SO4, filtered and concentrated. The crude residue was co-evaporated with heptane (2x) and purified by flash chromatography on a BiotageTM snap 340g silica cartridge, using a gradient of EtOAc (0-25%) in Hex as eluent. The fractions were combined and concentrated to provide thetitle compound (18.0 g, 84% yield). ?H NMR (400 MHz, CDC13) oe 8.23 (s, 1H), 7.71 (s, 1H),4.51 (s, 2H), 3.85 (s, 3H), 2.25 (s, 3H).

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; VERTEX PHARMACEUTICALS INCORPORATED; GALLANT, Michel; TRUCHON, Jean-Francois; REDDY, Thumkunta, Jagadeeswar; DIETRICH, Evelyne; VAILLANCOURT, Louis; VALLEE, Frederic; (131 pag.)WO2016/199105; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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 1.0012 g (8.1228 mmol) of pyridine-2-carboxylic acid wasadded 15 mL of thionyl chloride and the reaction mixture wasstirred under reflux for 3 h. Then 1.3425 g (8.1270 mmol) of methyl-4-amino-3-methylbenzoate in 35 mL of chloroformwas added intothe obtained acid chloride. The reactants were stirred under refluxnext 2 h. After chloroform evaporation under vacuum a beigepowder precipitated:(1.5633 g, 5.7839 mmol, yield ca.: 71%, Anal. Calc. C15H14N2O3[%]: C, 66,66; H, 5,22; N, 10,36; Found: C, 66.33; H, 4.90; N, 10.22).The beige crystals occurred after the recrystallization procedurewith the use of 2-propanol. 1H NMR (600 MHz, CDCl3) delta 10.38-10.29 (m, 1H), 8.66-8.62 (m, 1H), 8.53 (d, J 8.5 Hz, 1H),8.31 (d, J 7.8 Hz, 1H), 7.98-7.95 (m, J 8.6 Hz, 1H), 7.95-7.90 (m,J 3.4 Hz, 1H), 7.51 (td, J 7.3, 4.9 Hz, 1H), 3.91 (s, 1H), 2.47 (s, 1H).13C NMR (151 MHz, CDCl3) delta 167.22, 162.35, 150.11, 148.53, 140.62,138.15, 132.11, 129.18, 127.13, 127.07, 125.77, 122.87, 120.01, 77.58,77.37, 77.16, 52.32, 17.96. FT-IR (KBr, cm-1): 3435 n(O-H KBr), 3342n(N-H), 3098, 3062, 2997, 2951, 2905, 2839 n(C-H), 1712, 1698n(C]O), 1609-1440 n(ringC]C), 1292-1095 n(C-O) and (C-N)overlapped, 769, 684, 622 d(C-H ringC]C)oop.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Skokowski, Przemys?aw; Gruszczy?ska, Joanna; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1178; (2019); p. 669 – 681;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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 stirred solution of methyl 4-amino-5-methylbenzoate (85) (2.48 g, 15 mmol) in 25 mL of AcOH, NBS (3.0 g, 17 mmol)was added portionwise, the mixture was stirred for 1 h, diluted with water, extracted with DCM, washed with a saturated NaHCO3 solution, dried over a2S04, and rotovapped to yield 3.66 g of methyl 4-amino-3-bromo-5-methylbenzoate (86). XH NMR (CDC13, 400 MHz) delta 8.03 (s, 1H), 7.71 (s, 1H), 4.50 (brs, 2H), 3.87 (s, 3H), 2.25 (s, 3H).

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IVACHTCHENKO, Alexandre, Vasilievich; ALLA CHEM, LLC; IVASHCHENKO, Andrey, Alexandrovich; SAVCHUK, Nikolay, Filippovich; MITKIN, Oleg, Dmitrievich; (98 pag.)WO2017/39791; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics