2-amino-N-methoxy-N-methylbenzamide

Base Information

• Chemical Name: 2-amino-N-methoxy-N-methylbenzamide
• CAS No.: 133776-41-7
• Molecular Formula: C9H12N2O2
• Molecular Weight: 180.206
• DSSTox Substance ID: DTXSID60453391
• Wikidata: Q82274522
• Mol file: 133776-41-7.mol

Synonyms:2-amino-N-methoxy-N-methylbenzamide;133776-41-7;2-amino-N-methoxy-N-methyl-benzamide;anthranilic acid N-methoxy-N-methylamide;SCHEMBL33252;DTXSID60453391;N-methoxy-N-methyl-anthranilamide;RIPUVVAYNHOONU-UHFFFAOYSA-N;N-methyl-N-methyloxy-2-aminobenzamide;SB32894;2-amino-N-methyl-N-(methyloxy)benzamide;anthranilic acid N-methoxyl-N-methylamide;AS-62305;N-methoxy-N-methyl anthranilic acid amide;CS-0131206;EN300-61925;W15320

Chemical Property of 2-amino-N-methoxy-N-methylbenzamide

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 180.089877630
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=O)C1=CC=CC=C1N)OC

Technology Process of 2-amino-N-methoxy-N-methylbenzamide

There total 5 articles about 2-amino-N-methoxy-N-methylbenzamide 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: 87.0%

isatoic anhydride (118-48-9) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → anthranilic acid N-methoxy-N-methylamide (133776-41-7)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 36h;

DOI:10.1002/bkcs.12239

Reference yield: 87.0%

2,2,2-trichloroethyl (2-(methoxy(methyl)carbamoyl)phenyl)carbamate → anthranilic acid N-methoxy-N-methylamide (133776-41-7)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 100 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;

DOI:10.1021/acs.joc.0c01789

Reference yield: 86.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → anthranilic acid N-methoxy-N-methylamide (133776-41-7)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; anthranilic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

N,O-dimethylhydroxylamine*hydrochloride; With triethylamine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/acs.joc.6b00212

upstream raw materials:

isatoic anhydride

N,O-dimethylhydroxylamine*hydrochloride

N,0-dimethylhydroxylamine

anthranilic acid

Downstream raw materials:

3'-cyano-2-aminobenzophenone

4-(2-aminobenzoyl)benzonitrile

(2-aminophenyl)-(3-methoxyphenyl)methanone

(2-aminophenyl)[4-(tert-butyl)phenyl]methanone

Refernces

• 1、 In Lee, Jae. "An Efficient Synthesis of (1-Methyl)-2-phenyl-4-quinolones from (N-Methyl)isatoic Anhydride". supporting information. p. 556 - 558. Retrieved 2021/02/09.
• 2、 Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min. "One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization". supporting information. p. 2438 - 2455. Retrieved 2020/01/31.