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

HRID 1586197Notes

Reaction equation

HRID 1586197 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-26a5d087c1b54a72b4a03ae63d898d70
Source dataset
uspto-grants-1999_08
Patent number
US05942536

Reaction notes

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