Acetonitrile → 3-Amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrile

HRID 2422705Notes

Reaction equation

HRID 2422705 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[C:12](#[N:14])[CH3:13].C1COCC1.CC(C)([O-])C.[K+]>C([O-])(O)=O.[Na+]>[NH2:6][C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1)=[CH:13][C:12]#[N:14]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran2×HCID 27745483-Fluoro-4-methoxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 671792423-Amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrileYield 78.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Combine 3-fluoro-4-methoxybenzonitrile (25.000 g, 165.563 mmol) and acetonitrile (13.576 g, 331.126 mmol) and THF (33 mL). Add potassium t-butoxide in THF (1 M, 182.1 mL, 182.1 mmol) with stirring. Stir overnight. Dilute with satd NaHCO3 and extract with EtOAc. Evaporate the organic solution and crystallize from hexane/EtOAc to afford 3-amino-3-(3-fluoro-4-methoxyphenyl)acrylonitrile. Yield: 78.6%. ES-MS: m/e 193.0 (m+1).

Workup

  1. extractionextract with EtOAc
  2. customEvaporate the organic solution
  3. customcrystallize from hexane/EtOAc

Sources & evidence

ORD record
ord-e428e4ef915245858f09fdd3dbb2c4f2
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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