Dimethylformamide → 3-Amino-4-methoxy-N-(3,4-dimethylphenyl)-benzamide

HRID 1859649Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[N+:18]([O-])=O.CN(C)C=O.[CH3:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH2:30]>>[NH2:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[O:8][CH3:7])[C:13]([NH:30][C:29]1[CH:31]=[CH:32][C:33]([CH3:34])=[C:27]([CH3:26])[CH:28]=1)=[O:15]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 72483,4-Dimethylaniline

HCID 65578Oxalyl chloride

HCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 167860273-Amino-4-methoxy-N-(3,4-dimethylphenyl)-benzamideYield 87.4%

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (3.0 mL, 34.4 mmol), 4-methoxy-3-nitrobenzoic acid (5.00 g, 25.36 mmol), dimethylformamide (1.0 mL, 12.92 mmol), and 3,4-dimethylaniline (6.2 g, 51 mmol) to afford the product (5.99 g); m.p. 138-142° C.

Workup

customPrepared

Sources & evidence

ORD record: ord-88b11054422b400c82e933811a6b0b36
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

Loading…