Category: 27492-84-8

Electric Literature of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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.

General procedure: A solution of the 4 (0.48 g, 2 mmol), 3-fluoroaniline (0.24g,2.2 mmol) in isopropanol (30 ml) were stirred at 90 C for 4 h.Isopropanol was removed under reduced pressure and the residuewas purified through a column chromatography on silica withchloroform/methanol (V:V 50:1) as a white solid (0.58 g, 91.8percentyield).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Deng, Cheng-Long; Li, Dan-Dan; Liu, Dan-Dan; Chai, Shao-Meng; Wang, Wei; Zhang, Yan; Chen, Kai; Li, Xin; Wang, Jian; Song, Shao-Jiang; Song, Hong-Rui; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 460 – 470;,
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27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C9H11NO3

Description 20: Methyl 4-{[(2-fluorophenyl)carbonyl]amino}-2-(methyloxy)benzoate; Methyl 4-amino-2-(methyloxy)benzoate (10.0 g, 55.2 mmol) was suspended in dichloromethane (50 ml_), cooled in an ice bath and treated dropwise with diisopropylethylamine (10.57 ml_, 60.8 mmol) followed by 2-fluorobenzoyl chloride (7.25 ml_, 60.8 mmol). The mixture was allowed to warm to room temperature and stirred under argon for 2.5 hours. The solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine. The ethyl acetate layer was separated. A solid came out of solution upon standing. This was collected by filtration to give the title compound. LC/MS (ES+ve): [M+H]+ at m/z 304 (C16H14FNO4 requires [M+H]+ at m/z 304).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/138033; (2007); A1;,
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Electric Literature of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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.

[0542] To a solution of 269-2 (14.4 g, 8 mmol) in EtOH (120 mL) was added acetic anhydride (9.0 g, 88 mmol). The mixture was allowed to stir at 50 °C for 2 h. The mixture was cooled to r.t., and neutralized with aqueous NaHC03 solution. The mixture was extracted with EA (3 x 60 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-3 (15.0 g. 84.1 percent). +ESI-MS:m/z 223.9 [M+H]+.

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-2-methoxybenzoate, its application will become more common.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Ester – Wikipedia,
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27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of Methyl 4-amino-2-methoxybenzoate

(2) the above-mentioned the resulting 4-amino-2-methoxybenzoic acid methyl ester and N-chloro succinimide the mole ratio is that 1:1 in 70 C stirring in DMF solution of 3 hours later, is poured into the ice water is separated out in solid, filtering and drying to obtain 1.70 kg of 4-amino-5-chloro-2-methoxybenzoic acid methyl ester, in the yield of 88.3%.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Ma, Kefeng; Ren, Yu; Pan, Xiongfei; Wu, Jiating; Xu, Tongqiang; (6 pag.)CN105237422; (2016); A;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step c) 4-[(Biphenyl-2-carbonyl)-amino]-2-methoxybenzoic acid methyl ester Into a refluxing solution of 2-biphenylcarboxylic acid (9.2 g, 46 mmol) in dichloromethane was added dimethylformamide (0.1 ml, 1.4 mmol) and then neat oxalyl chloride (8.1 ml, 92 mmol) via syringe. The reaction was refluxed for 10 min, then the volatiles removed in vacuo. The residue was redissolved in dichloromethane, concentrated and dried under high vacuum for 15 min. The acid chloride was dissolved in dichloromethane (50 ml) and added into a 0° C. solution of 4-amino-2-methoxy-benzoic acid methyl ester (8.4 g, 46 mmol), diisopropyl ethylamine (10.5 ml, 60 mmol) and dichloromethane (200 ml). The reaction was warmed to room temperature and stirred for 16 hours. The reaction was diluted with dichloromethane, washed with water, (1N) sodium hydroxide (1N) HCl and brine, and dried (MgSO4). Evaporation gave a yellow foam, which was crystallized from methanol to give a light yellow solid (16.08 g, 96percent) m.p. 141°-142° C. Analysis for: C22 H19 N O4 Calcd: C, 73.12; H, 5.30; N, 3.88. Found: C, 72.93; H, 5.20; N, 3.83.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US5753648; (1998); A;,
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Application of 27492-84-8, 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. 27492-84-8 name is Methyl 4-amino-2-methoxybenzoate, 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.

To a solution of methyl 4-amino-2-methoxybenzoate (2.0 g, 0.0 11 mol) in DCM (50 mL) cooled to 0 C was added triethylamine (3.0 mL, 0.022 mol) and the reaction mixture was stirred for 10 minutes. Acetyl chloride (1.3 g, 0.0 165 mol) was addeddropwise and the reaction was stirred for 3 h. Water (50 mL) was added and the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and volatiles were evaporated to dryness under reduced pressure to give methyl 4-acetamido-2-methoxybenzoate (2.3 g, 0.01 mol, 91% yield) as a light brown solid. ?H NMR (400 MHz, DMSO-d6) oe 10.22 (s,1H), 7.66 (d, J= 8.8 Hz, 1H), 7.47 (d, J= 1.6 Hz, 1H), 7.20 (dd, J 8.4, 2.0 Hz, 1H),3.74-3.79 (m, 6H), 2.07 (s, 3H); LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14NO4, 224.08]; LC/MS retention time (method B): ti = 1.20 mm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); A1;,
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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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27492-84-8

Synthesis of 4-(2-Chloro-ethylamino)-2-methoxy-benzoic acid methyl ester 16; Methyl 4-amino-2-methoylbenzoate (2 g, 11.04 mmol, 1 eq) was dissolved in methanol (30 ml) and a 1:1 mixture (2 ml) of 6M aq. HCl and methanol was added. Chloroacetaldehyde (50percent in water, 2.08 ml, 13.27 mmol, 1.2 eq) was added and the mixture was cooled to 0° C. NaBH3CN (0.78 g, 12.37 mmol, 1.12 eq) was added in portions over 2 min and the mixture was stirred for 5 days at ambient temperature. The mixture was poured into sat. aq. NaHCO3 (100 ml) and DCM (100 ml) was added, the pH was adjusted to 7-8 with dil. aq. HCl and the organic layer was poured off. The aqueous layer was then extracted with DCM (2.x.50 ml) and the combined organic layers were washed with water (2.x.100 ml), were washed with brine (50 ml), were dried over Na2SO4, filtered and the solvent was removed in vacuo. The product was purified via column chromatography eluted with a gradient from 1:1 to 1:3 CyH:EtOAc (Rf product=0.5, Rf SM=0.35 in 1:3 CyH:EtOAc, UV, KMnO4). This gave 1.968 g (73percent) of white solid. 1H-NMR (CDCl3) 500 MHz: delta (ppm)=3.55 (2H, br.quart, J=5.1 Hz, ClCH2CH2), 3.71 (2H, t, J=5.9 Hz, ClCH2CH2), 3.82 (3H, s, COCH3), 3.86 (3H, s, COOCH3), 4.48 (1H, br.s, ClCH2CH2NH), 6.13 (1H, d, J=1.9 Hz, CCHCN), 6.19 (1H, dd, J=2.0 Hz, J=8.6 Hz, CCHCHCN), 7.77 (1H, d, J=8.6 Hz, CCHCHCN). 13C-NMR (CDCl3) 125 MHz: delta (ppm)=43.1 (CH2), 44.8 (CH2), 51.4 (CH3), 55.8 (CH3), 96.1 (CH), 104.1 (CH), 108.8 (C), 134.3 (CH), 152.2 (C), 161.8 (C), 166.1 (CO). IR Spectrum; evaporated film: v(cm-1)=3361, 2950, 2840, 1700, 1607, 1526, 1346, 1255, 1182, 1085. MS-ES (negative): 242.1 (M-H+), 244.1 (M-H+). MS-ES (positive): 244.1 (M+H+), 246.1 (M+H+).

According to the analysis of related databases, 27492-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Desreumaux, Pierre; Bellinvia, Salvatore; Chavatte, Philippe; Baroni, Sergio; US2011/39808; (2011); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-2-methoxybenzoate

Method 2A mixture of methyl 4-amino-2-methoxybenzoate (10.8 g, 59.6 mmol), the product from step(i) above (20.09 g, 54.2 mmol) and potassium carbonate (15 g, 109 mmol) in DMF (300 mL)was degassed with N2 for 10 mm. BrettPhos G3 precatalyst(1 g, 1.103 mmol) was added andthe mixture heated at 85°C for 3 h. The mixture was cooled then partitioned between DCM(500 mL) and water (800 mL). The organic layer was washed with water (500 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was triturated with ether, filtered and dried to afford the sub-title compound (21.7 g) as a grey solid. 1H NMR (400 MHz, DMSO-d6) O 9.38 (s, IH), 9.36 (s, IH), 8.18 (d, IH), 8.14 (d, IH), 7.83 (d,IH), 7.54-7.66 (m, 5H), 7.38 (d, IH), 7.22 (dd, IH), 6.69 (dd, IH), 6.14 (d, IH), 3.74 (s, 3H),3.71 (s, 3H), 1.53 (s, 9H).LCMS m/z 516 (M+H) (ES)

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew Colin Thor; (62 pag.)WO2016/51188; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11NO3

Step 1Methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoateProcedure:A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (600 mg, 2.4 mmol), methyl 4-amino-2-methoxybenzoate (362 mg, 2 mmol), EDCI (764 mg, 4 mmol) and DMAP (488 mg, 4 mmol) in 10 mL of DMF was stirred at room temperature for 38 hours.The mixture was poured into water and extracted with EtOAc (3*15 mL).The organic layer was washed with brine and dried over Na2SO4.After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with (petroleum ether_EtOAc=4:1) to give methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (180 mg, 22percent) as solid. 1H NMR (300 MHz, CD3OD): delta 8.31 (s, 1H), 8.05-8.01 (m, 1H), 7.97-7.94 (m, 1H), 7.81 (d, 1H, J=8.7 Hz), 7.71 (d, 1H, J=1.8 Hz), 7.53 (d, 1H, J=7.5 Hz), 7.37 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 3.91 (s, 3H), 3.85 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H11NO3

To a stirred solution of methyl 4-amino-2-methoxybenzoate (10 g, 55 mmol) in dichloromethane (100 mL) was added triethylamine (15.4 mL, 110 mmol) at 0 C and the mixture was stirred for 15 mm. To this mixture, acetyl chloride (5.68 g, 71 mmol) was added drop wise and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of water (75 mL). The organiclayer was separated, washed with brine solution (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford methyl 4-acetamido-2- methoxybenzoate (13.0 g, 58.2 mmol, quantitative yield) as a yellow solid: LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14N04, 224.1]; LC/MS retention time (method B): tR = 1.21 mm.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; MACOR, John E.; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; WO2015/6100; (2015); A1;,
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