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

HRID 726337Notes

Reaction equation

HRID 726337 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.[H][H]>O1CCCC1.[Pt]>[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

5

Reactant 2

HCID 39484284-fluoro-N-(4-nitrophenyl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 10988055N-(4-Aminophenyl)-4-fluorobenzamideYield 98.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 56.6 gm (0.217 mole) 4-(4-fluorobenz-oyl)aminonitrobenzene in 875 mL tetrahydrofuran were added 5.7 gm 5% platinum on carbon. The reaction mixture was hydrogenated at room temperature for 18 hours at initial hydrogen pressure of 60 p.s.i. The reaction mixture was then filtered and the filtrate concentrated under reduced pressure to give 49.3 gm (98.5%) of the desired compound.

Workup

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

Sources & evidence

ORD record
ord-ccf2297eda5a41cc90426f03eaece458
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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