Dimethylformamide → 3-Amino-4-methoxy-N-(3,5-dimethylphenyl)-benzamide

HRID 1387503Notes

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]=[C:32]([CH3:34])[CH:33]=1)[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]=[C:32]([CH3:34])[CH:33]=[C:27]([CH3:26])[CH:28]=1)=[O:15]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 79493,5-Dimethylaniline

HCID 65578Oxalyl chloride

HCID 666404-Methoxy-3-nitrobenzoic acid

Product 1

HCID 167939593-Amino-4-methoxy-N-(3,5-dimethylphenyl)-benzamideYield 69.9%

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (3.0 mL, 4.39 mmol), 4-methoxy-3-nitrobenzoic acid (5.00 g, 25.36 mmol), dimethylformamide (0.5 mL, 6.5 mmol), and 3,5-dimethylaniline (6.4 mL, 51.33 mmol) to afford the product (4.79 g); m.p. 155-162° C.

Workup

customPrepared

Sources & evidence

ORD record: ord-ec79dc536bd541a39f2a3bc96eb9db59
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268387B1

Reaction notes

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