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

HRID 843967Notes

Reaction equation

HRID 843967 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-2d328f7503eb43be898ea5c2acc8cd3d
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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