Water → 2-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrile

HRID 610044Notes

Reaction equation

HRID 610044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12]C(=O)C)[C:9](=O)[CH3:10].[C:16](#[N:20])[CH2:17][C:18]#[N:19].[OH-].[K+].O>CO>[NH2:19][C:18]1[NH:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[C:9]([CH3:10])[C:17]=1[C:16]#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 14797Potassium HydroxideHCID 22111313N-(1-(2-fluorophenyl)-2-oxopropyl)acetamide

Product 1

HCID 101767492-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrileYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Fluorophenyl)-1-acetamido-2-propanone (3.13 g) and malononitrile (1.49 g) were dissolved in methanol (15 ml) and the solution was stirred under ice-cooling. Then, 55% aqueous solution of potassium hydroxide was added to the above solution to adjust to pH 10. The reaction mixture was then warmed and stirred at 55-60° C. for 0.5 hour. After cooling, the reaction mixture was poured into iced water and the resulting crystals were collected by filtration. This crude crystalline product was recrystallized from methanol-water and, further, from benzene to provide the title compound as colorless crystals (0.72 g). m.p. 117-118° C.

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was then warmed
  3. stirringstirred at 55-60° C. for 0.5 hour
  4. temperatureAfter cooling
  5. filtrationthe resulting crystals were collected by filtration
  6. customThis crude crystalline product was recrystallized from methanol-water

Sources & evidence

ORD record
ord-6cc8e90de2fb4351afb9e470ee337969
Source dataset
uspto-grants-1999_12
Patent number
US05998459

Reaction notes

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