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

HRID 1738159Notes

Reaction equation

HRID 1738159 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-3e57512455cd47dd92c26e9c589e4fe3
Source dataset
uspto-grants-1999_10
Patent number
US05962473

Reaction notes

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