(3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone → (4-Amino-3-fluorophenyl)pyrrolidin-1-ylmethanone

HRID 18607Notes

Reaction equation

HRID 18607 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 1

HCID 55103417(3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone

Product 1

HCID 11252765(4-Amino-3-fluorophenyl)pyrrolidin-1-ylmethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

515.0 mg (2.16 mmol) (3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone were dissolved in 20 mL MeOH. The solution was evacuated and rinsed with argon several times. 150 mg palladium on charcoal (10%) were added and again the mixture was evacuated and rinsed with argon several times. Finally argon was exchanged by hydrogen (balloon filled with hydrogen) and the mixture was stirred for 2 h at room temperature. The reaction mixture was filtered over “Celite” and the filter residue was washed with 30 mL MeOH. The filtrate was concentrated under vacuo to give pure (4-Amino-3-fluoro-phenyl)-pyrrolidin-1-yl-methanone as a colorless oil.

Workup

  1. customThe solution was evacuated
  2. washrinsed with argon several times
  3. addition150 mg palladium on charcoal (10%) were added
  4. customagain the mixture was evacuated
  5. washrinsed with argon several times
  6. filtrationThe reaction mixture was filtered over “Celite”
  7. washthe filter residue was washed with 30 mL MeOH
  8. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-31c443897ac34bfcab65cf5d9077499b
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

Loading…