Dichloromethane → 3-Fluoro-4-(pyrrolidin-1-yl)aniline

HRID 56138Notes

Reaction equation

HRID 56138 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][CH2:12]1.C(Cl)Cl>[Pd].CO>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[NH2:8]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 28721221-(2-Fluoro-4-nitrophenyl)pyrrolidine

Product 1

HCID 65005243-Fluoro-4-(pyrrolidin-1-yl)anilineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(2-fluoro-4-nitrophenyl)pyrrolidine (1.60 g, 7.62 mmol) in mixed solvents of CH2Cl2 (20 mL) and MeOH (20 mL) was added catalyst Pd/C (0.16 g). The reaction was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V) 5:1) to give the title compound as a white solid (1.20 g, 88%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V) 5:1)

Sources & evidence

ORD record
ord-91a11532f7e34b58af46186517edeccc
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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