4-Nitrobenzoic Acid → N-(3-methoxyphenyl)-4-nitrobenzamide

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:18])=[CH:20][CH:21]=1)([O-:12])=[O:11]

Participants

Reactant 2

HCID 61084-Nitrobenzoic Acid

HCID 108243-Methoxyaniline

Product 1

HCID 774514N-(3-methoxyphenyl)-4-nitrobenzamideYield 93.2%

Procedure

Using m-anisidine (2.50 g, 15.0 mmol) and 4-nitrobenzoic acid (2.03 g, 16.5 mmol), the procedure of Reference Example 16 was repeated to obtain 3.80 g (93.2%) of the title compound in the form of light yellow needle crystals.

Sources & evidence

ORD record: ord-b82805e2b34b4ecf82e3f2502d0befca
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Reaction notes

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