Dimethylformamide → 3-Amino-4-methoxy-N-(4-methoxyphenyl)-benzamide

HRID 1387497Notes

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

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7732P-Anisidine

HCID 65578Oxalyl chloride

HCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 167904313-Amino-4-methoxy-N-(4-methoxyphenyl)-benzamideYield 64.4%

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (3.0 mL, 34.39 mmol), 4-methoxy-3-nitrobenzoic acid (5.00 g, 25.36 mmol), dimethylformamide (0.5 mL, 6.5 mmol), and 4-methoxyaniline (6.25 g, 50.7 mmol) to afford the product (4.45 g); m.p. 164-167° C.

Workup

customPrepared

Sources & evidence

ORD record: ord-3904b326945a4bac9d649eba51cc5e6e
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268387B1

Reaction notes

Loading…