4-Nitrobenzoic Acid → 4'-Fluoro-4-nitrobenzanilide

Reaction equation

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

Participants

Reactant 2

HCID 61084-Nitrobenzoic Acid

HCID 97314-Fluoroaniline

Product 1

HCID 3065684'-Fluoro-4-nitrobenzanilideYield 65.8%

Procedure

Using 4-fluoroaniline (1.0 ml, 9.93 mmol) and 4-nitrobenzoic acid (1.58 g, 9.36 mmol), the procedure of Reference Example 16 was repeated to obtain 1.60 g (65.8%) of the title compound in the form of light yellow needle crystals.

Sources & evidence

ORD record: ord-6dae5ade71d64ef5bed47b84c6e2b2bc
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Reaction notes

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