Ammonia methanol → 5-(3-fluorophenyl)-3,4-dihydro-2H-pyrrole

HRID 1594688Notes

Reaction equation

HRID 1594688 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.CO.N>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][CH2:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 217067514-(3-Fluorophenyl)-4-oxobutanenitrile

Product 1

HCID 120090495-(3-fluorophenyl)-3,4-dihydro-2H-pyrroleYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-Fluoro-phenyl)-4-oxo-butyronitrile (1.60 g, 9.03 mmol) dissolved in MeOH (45 ml) and 3.5 N MeOH-NH3 (45 ml) was hydrogenated on Ra-Ni at RT for 16 h. The catalyst was filtered off, the filtrate evaporated and the crude product purified by column chromatography on silica gel (ethyl acetate/toluene 1:2) to give the product (1.16 g, 79%) as a colorless oil, MS: m/e=163 (M+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customthe crude product purified by column chromatography on silica gel (ethyl acetate/toluene 1:2)

Sources & evidence

ORD record
ord-d5f715335c7d4136ac59f9422aca5eaf
Source dataset
uspto-grants-2001_09
Patent number
US06284785B1

Reaction notes

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