Category: 36692-49-6

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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, A new synthetic method of this compound is introduced below., Product Details of 36692-49-6

General procedure: Substituted 1,2-phenylenediamines (1 mmol) and substituted phenacyl bromides (1 mmol) were dissolved in acetonitrile (5 ml). To this solution, K10-Mont. clay (50 mg) was added and heated at 50 C for 3 h. After completion, the reaction mixture was filtered to remove the catalyst and washed with ethyl acetate (10 mL). The filtrate was concentrated and the residue was purified by column chromatography using hexane:ethyl acetate (15 % ethyl acetate in hexane) as an eluent to afford quinoxaline derivatives in high yields. The recovered catalyst was thoroughly washed with ethyl acetate, air dried, activated at 80 C for 3 h and reused for successive runs. The purified products are characterized by their 1H, 13C NMR as well as by mass spectral data

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:
Article; Jeganathan, Mariappan; Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi; Tetrahedron Letters; vol. 55; 9; (2014); p. 1616 – 1620;,
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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

Reference of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl (4-fluorophenyl)(oxo)acetate (50.0 g, 275 mmol) and methyl 3,4- diaminobenzoate (46.9 g, 282 mmol) in ethanol (2.5 L) was heated to reflux for 2 d. The mixture was cooled to rt and most of the ethanol was removed in vacuo to form a thick paste. 0.5 L of THF was added to get a stirrable slurry and the slurry was stirred for 1 h, diluted further with 1 L of ether and solid was collected by filtration (50.0 g, 76.3%) as a mixture of regioisomers.To a solution of methyl 2-(4-fluorophenyl)-3-oxo-3,4-dihydroquinoxaline-6-carboxylate(50.0 g, 168 mmol) (mixture of regioisomers) in THF (0.9 L) and methanol (0.9 L) at rt was added 2.0 M of sodium hydroxide in water (300 mL). The reaction mixture was stirred at 70 C for 2 h. The mixture was allowed to cool slightly and some solids formed. The reaction mixture was filtered while warm to afford a clear orange solution. The filtrate was stirred with mechanic stirring. IN HC1 aqueous solution (~ 450 rtiL) was slowly added (over 15 min) to pH=8. The suspension was stirred for 5 min, filtered, washed with 100 mL of 1:1 MeOH:THF, dried to give a light yellow solid. [In some cases, there is still some undesired isomer present at this point. If so, the material was redissolved in methanol/THF mixture (14 mL per gram of each solvent) and 1 N NaOH (4.2 equivalents), and then reprecipitated to pH = 8 using 1 N HC1. This dissolution/reprecipitation procedure can be repeated until the pure desired regioisomer is obtained.] To the solid was added 300 mL of methanol, 300 mL of THF, and 250 mL of IN NaOH and the resulting solution was stirred by mechanical stirring until dissolved. The resulting solution was adjusted to pH=2.5 by adding IN HC1. The precipitate was collected by filtration, transferred to a round bottom flask using MeOH, evaporated in vacuo, and azeotroped with MeCN. The resulting solid was dried in vacuum pump to give a pure acid product (26.3 g, 55.2%) as a beige powder. LCMS (ESI+): m/z = 285.0 (M+H). H NMR (400 MHz, DMSO-6) delta 13.34 (s, 1H), 12.76 (s, 1H), 8.44 (dd, J= 9.1, 5.8 Hz, 2H), 7.96 – 7.89 (m, 2H), 7.83 (dd, J= 8.4, 1.8 Hz, 1H), 7.35 (t, J= 9.0 Hz, 2H).

The synthetic route of Methyl 3,4-diaminobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; GIGSTAD, Kenneth, M.; CARDIN, David, P.; HIRAYAMA, Takaharu; HIROSE, Masaaki; HU, Yongbo; KAKEI, Hiroyuki; LEE, Hong, Myung; MOTOYAJI, Takashi; NII, Noriyuki; SHI, Zhan; VYSKOCIL, Stepan; WATANABE, Hiroyuki; WO2015/161142; (2015); A1;,
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Related Products of 36692-49-6, 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. 36692-49-6 name is Methyl 3,4-diaminobenzoate, 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.

Typical procedure: Mix Et3N (2.53 mg, 0.025 mmol), 2-phenylacetaldehyde 1a (30 mg, 0.25 mmol), benzene-1,2-diamine 2a (32.4 mg, 0.3 mmol), in toluene (2.5 mL) under O2 (1 atm). The reaction mixture was stirred at 60 C for 12 h. After cooling down to room temperature and concentrating in vacuum, the residue was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate=20:1) to afford 47 mg (91%) of 3aa.

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

Reference:
Article; Zhang, Chun; Xu, Zejun; Zhang, Liangren; Jiao, Ning; Tetrahedron; vol. 68; 26; (2012); p. 5258 – 5262;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 36692-49-6, 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 36692-49-6 as follows.

Example 96; (2Z,5Z)-2-[(2,6-dichlorophenyl)imino]-5-{[2-(1-methylethyl)-1H-benzimidazol-6-yl ]methylidene}-1,3-thiazolidin-4-one; (a) methyl 2- (1-methylethyl)-lHbenzimidazole-6-carboxylate; A solution of isobutyraldehyde (0.22 mL, 2.41 mmol) and 40 % aq. sodium hydrogen sulfite (2.6 mL) was stirred at room temperature for 1 h. To this mixture is added a solution of methyl 3,4-diaminobenzoate (0.400 g, 2.41 mmol) in ethanol (2 mL). The resulting solution is heated to reflux overnight. The mixture was diluted in water and the resulting precipitate was collected by filtration to obtain 0.524 g of the desired product in >99 % yield. The crude was used without further purification. [MS (ES+) m/e 219 M+H] +. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 8.30 (d, =7=1. 0 Hz, 1 H) 7.93 (dd, J=8. 6,1. 5 Hz, 1 H) 7.54 (d, 8. 6 Hz, 1 H) 3.90 (s, 3 H) 3.30-3. 41 (m, 1 H) 1. 48 (d, 7. 1 Hz, 6 H).

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/82901; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 36692-49-6, 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In 25 ml round-bottomed flask, a mixture of 1,2-phenylendiamine (1 mmol), a-bromoacetophenone(1 mmol) and BAILnano-SiO2 catalyst (35 mol%) was preparedand the reaction mixture was stirred at room temperature for the time shown inTable 2. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate (5 mL) was added and the catalyst was separated by simplefiltration. The residue was dried over anhydrous Na2SO4 and after evaporation ofsolvent the pure product was obtained by recrystallization from ethanol.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,4-diaminobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Daragahi, Seyed Arash Hosseini; Mohebat, Razieh; Mosslemin, Mohammad Hossein; Organic Preparations and Procedures International; vol. 50; 3; (2018); p. 301 – 313;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

36692-49-6, name is Methyl 3,4-diaminobenzoate, 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. Product Details of 36692-49-6

A mixture of (4-tert-butyl-phenoxy)acetic acid (300 mg, 1.4 mmol), 3,4-diaminobenzoic acid methyl ester (300 mg, 1.4 mmol) in PPSE (4.8 mL) was heated at 160 C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane=1:9-4:6) to afford 2-2,4-tert-butyl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (547 mg, 80% yield). 1H-NMR (CDCl3, 300 MHz) 8.39 (1H, s, aromatic), 8.03 (1H, d, J=8.1 Hz, aromatic), 7.66 (1H, d, J=7.8 Hz, aromatic), 7.27 (2H, d, J=8.4 Hz, aromatic), 6.88 (2H, d, J=8.7 Hz, aromatic), 5.43 (2H, s, OCH2), 3.95 (3H, s, OCH3), 1.27 (9H, s, t-butyl), NH not detected.

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

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 36692-49-6

Step 450b. The mixture of (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (5 g, 23.2 mmol) in acetonitrile (40 mL) was added 1,1?-carbonyldiimidazole (3.95 g, 24.5 mmol). The resulting mixture was stirred at room temperature for 20 min before being added methyl 3,4-diaminobenzoate (3.86g, 23.2 mmol). The solution was stirred at room temperature for another 3 hours before being partitioned between water and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown slurry, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow oil (8.14g, 98%). ESIMS m/z=364.17 [M+H]+. ; Step 450c. The solution of compound from step 450b in acetic acid (150 mL) was stirred at 60 C. for three days before all volatiles were removed. The resulting residue was partitioned between aqueous NaHCO3 and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown oil, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow solid (2.02 g, 28%). ESIMS m/z=346.15 [M+H]+.

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

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Qiu, Yao-Ling; Wang, Ce; Peng, Xiaowen; Ying, Lu; Or, Yat Sun; US2020/2314; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics