Methyl 3-amino-4-butyramido-5-methylbenzoate

Base Information

• Chemical Name: Methyl 3-amino-4-butyramido-5-methylbenzoate
• CAS No.: 675882-71-0
• Molecular Formula: C13H18N2O3
• Molecular Weight: 250.298
• Hs Code.: 2924299090
• European Community (EC) Number: 614-084-7
• DSSTox Substance ID: DTXSID70435380
• Nikkaji Number: J1.644.605J
• Wikidata: Q72489049
• Mol file: 675882-71-0.mol

Synonyms:675882-71-0;Methyl 3-amino-4-butyramido-5-methylbenzoate;Methyl 3-amino-4-butanamido-5-methylbenzoate;methyl 3-amino-4-(butanoylamino)-5-methylbenzoate;Methyl 4-(butyrylamino)-5-methyl-3-aminobenzoate;SCHEMBL158750;DTXSID70435380;METHYL 5-AMINO-4-(BUTYRYLAMINO)-3-METHYLBENZOATE;UITANFWKOFOWHF-UHFFFAOYSA-N;BCP31024;AKOS015889983;CS-0245847;FT-0658741;Methyl3-amino-4-butyramido-5-methylbenzoate;EN300-312369;methyl 3-amino-4-(butyramido)-5-methylbenzoate;Methyl 3-amino-4-(butyrylamino)-5-methylbenzoate;3-Amino-4-butyrylamino-5-methylbenzoic acid methyl ester;3-Methyl-4-butyrylamido-5-aminobenzoic acid methyl ester;Benzoic acid,3-amino-5-methyl-4-[(1-oxobutyl)amino]-,methyl ester;Methyl-4-(butyrylamino)-3-methyl-5-aminobenzoate

Chemical Property of Methyl 3-amino-4-butyramido-5-methylbenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.581
• Boiling Point: 447.456 °C at 760 mmHg
• PKA: 14.16±0.70(Predicted)
• Flash Point: 224.414 °C
• PSA: 81.42000
• Density: 1.181 g/cm³
• LogP: 2.75660
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 250.13174244
• Heavy Atom Count: 18
• Complexity: 307

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl3-Amino-4-butanamido-5-methylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)NC1=C(C=C(C=C1C)C(=O)OC)N
• Uses: Methyl 3-Amino-4-butanamido-5-methylbenzoate can be used as an intermediate in the synthesis of compounds with medicinal applications.

Technology Process of Methyl 3-amino-4-butyramido-5-methylbenzoate

There total 5 articles about Methyl 3-amino-4-butyramido-5-methylbenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.8%

4-butyrylamino-3-methyl-5-nitro-benzoic acid methyl ester (152628-01-8) → 3-methyl-4-butyrylamino-5-aminobenzoic acid methyl ester (675882-71-0)

Guidance literature:

4-butyrylamino-3-methyl-5-nitro-benzoic acid methyl ester; With iron hydroxide oxide; pyrographite; In methanol; at 65 ℃; for 0.5h;

With hydrazine hydrate; for 6h; Reagent/catalyst; Solvent; Temperature;

Reference yield:

methyl 4-amino-3-methylbenzoate (18595-14-7) → 3-methyl-4-butyrylamino-5-aminobenzoic acid methyl ester (675882-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 79.6 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °C

2: 75.6 percent / nitric acid / 1.5 h / -20 - -15 °C

3: 92 percent / aq. hydrazine / Raney Ni / methanol / 20 °C

With nitric acid; hydrazine hydrate; triethylamine; nickel; In methanol; dichloromethane;

DOI:10.1002/jhet.5570400623

Reference yield:

methyl 4-(n-butyrylamino)-3-methylbenzoate (301533-59-5) → 3-methyl-4-butyrylamino-5-aminobenzoic acid methyl ester (675882-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75.6 percent / nitric acid / 1.5 h / -20 - -15 °C

2: 92 percent / aq. hydrazine / Raney Ni / methanol / 20 °C

With nitric acid; hydrazine hydrate; nickel; In methanol;

DOI:10.1002/jhet.5570400623

upstream raw materials:

4-butyrylamino-3-methyl-5-nitro-benzoic acid methyl ester

3-methyl-4-nitrobenzoic acid

methyl 4-amino-3-methylbenzoate

methyl 3-methyl-4-nitrobenzoate

Downstream raw materials:

4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid

4'-[4-methyl-6-(7-methyl-benzooxazol-2-yl)-2-propyl-benzoimidazol-1-ylmethyl]-biphenyl-2-carbonitrile

4'-[[2-n-propyl-4-methyl-6-(5-methylbenzoxazol-2-yl)-benzimidazol-1-yl]methyl]-2-cyanobiphenyl

methyl 4'-[[2-n-propyl-4-methyl-6-(5-methylbenzoxazol-2-yl)-benzimidazol-1-yl]methyl]biphenyl-2-carboxylate

Refernces

• 1、 Gallou, Fabrice,Li, Xiaohan,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.. "High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates". supporting information. p. 8114 - 8118. Retrieved 2021/10/25.
• 2、 Wu, Zhuo,Bao, Xiao-Lu,Zhu, Wei-Bo,Wang, Yan-Hui,Phuong Anh, Nguyen Thi,Wu, Xiao-Feng,Yan, Yi-Jia,Chen, Zhi-Long. "Design, Synthesis, and Biological Evaluation of 6-Benzoxazole Benzimidazole Derivatives with Antihypertension Activities". . p. 40 - 43. Retrieved 2019/01/14.