3-Fluoro-1-nitro-4-(1H-pyrrol-1-yl)benzene → 3-fluoro-4-(1H-pyrrol-1-yl)aniline

HRID 56129Notes

Reaction equation

HRID 56129 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[CH:15]=[CH:14][CH:13]=[CH:12]1>C(Cl)Cl.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[NH2:8]

Participants

4

Reactant 1

HCID 107034583-Fluoro-1-nitro-4-(1H-pyrrol-1-yl)benzene

Product 1

HCID 105834103-fluoro-4-(1H-pyrrol-1-yl)anilineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-fluoro-4-nitrophenyl)-1H-pyrrole (2.00 g, 9.70 mmol) in CH2Cl2 (35 mL) was added catalyst Pd/C (0.20 g). The reaction mixture was stirred at rt under H2 for 5 h, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=3:1) to give the title compound as a white solid (1.30 g, 76%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=3:1)

Sources & evidence

ORD record
ord-117a434a35fe4e83bd2b29ffc765144c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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