4-fluoro-N-(4-nitrophenyl)benzamide → N-(4-Aminophenyl)-4-fluorobenzamide

HRID 610666Notes

Reaction equation

HRID 610666 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1>[Pt].O1CCCC1>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 39484284-fluoro-N-(4-nitrophenyl)benzamide

Product 1

HCID 10988055N-(4-Aminophenyl)-4-fluorobenzamideYield 79%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 32.25 gm (124 mMol) N-(4-fluorobenzoyl)-4-nitroaniline and 3.2 gm platinum on carbon in 500 mL tetrahydrofuran was hydrogenated at room temperature for 18 hours with an initial pressure of 60 p.s.i. The reaction mixture was then filtered and the filtrate concentrated under reduced pressure to give 22.45 gm (79%) of N-(4-fluorobenzoyl)-4-aminoaniline.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-c87bf4664e674f879edf777b3085544f
Source dataset
uspto-grants-1999_12
Patent number
US05998630

Reaction notes

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