1-(2-Fluoro-4-nitrophenyl)-2-pyrrolidinone → 1-(4-Amino-2-fluorophenyl)pyrrolidin-2-one

HRID 1670476Notes

Reaction equation

HRID 1670476 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16]>CO.C1COCC1.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 534339651-(2-Fluoro-4-nitrophenyl)-2-pyrrolidinone

Product 1

HCID 521913851-(4-Amino-2-fluorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

650 mg (2.9 mmol) of 1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-2-one (Example 14b) and 65 mg of Pd/C 10% are shacked in 15 ml of MeOH/THF (1:1) under 1.1 bar of H2 for 2 h at rt. After completion of the reaction, the catalyst is filtered-off and the filtrate is evaporated in vacuo to give the title compound as an off-white solid. ES-MS: 195 (M+H)+; analytical HPLC: tret=1.91 minutes (Grad 1).

Workup

  1. customAfter completion of the reaction
  2. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-275036b4c38741a59ff5ea19b964edec
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

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