2-Nitroaniline → 4-methoxy-N-(2-nitrophenyl)benzamide

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11](Cl)(=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])=[O:20])=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 69462-Nitroaniline

HCID 7477p-Anisoyl chloride

Product 1

HCID 3460424-methoxy-N-(2-nitrophenyl)benzamide

Procedure

Using a procedure similar to Example 1B except starting with 2-nitroaniline and p-anisoyl chloride, the title compound was obtained as a solid (98%); MS(FD): 272.0.

Sources & evidence

ORD record: ord-8871996de56e4b848936ec925425ea44
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677369B2

Reaction notes

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