Acetonitrile → 3-Amino-3-(4-fluorophenyl)acrylonitrile

HRID 918232Notes

Reaction equation

HRID 918232 reaction equation
[Na].[C:2](#[N:4])[CH3:3].[F:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1>O>[NH2:11][C:10]([C:9]1[CH:12]=[CH:13][C:6]([F:5])=[CH:7][CH:8]=1)=[CH:3][C:2]#[N:4]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 145174-FluorobenzonitrileHCID 5360545Sodium

Product 1

HCID 573643293-Amino-3-(4-fluorophenyl)acrylonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure of Example 1 was used to react 2.7 grams (0.117 mole) of sodium and 5.2 grams (0.126 mole) of acetonitrile with 10.0 grams (0.083 mole) of p-fluorobenzonitrile. After the addition of water, the reaction mixture was extracted three times with chloroform. The combined chloroform extracts were concentrated to obtain a dark-colored crystalline mass which was recrystallized four times from a mixture of chloroform and hexane to obtain yellow plates of β-amino-β-(p-fluorophenyl)acrylonitrile, mleting point 110°-112°C. Analysis: -- Calculated for C9H7N2F (percent): C, 66.66; H, 4.35; N, 17.27; F, 11.72. Found (percent): C, 66.48; H, 4.34; N, 17.21; F, 11.19.

Workup

  1. extractionthe reaction mixture was extracted three times with chloroform
  2. concentrationThe combined chloroform extracts were concentrated
  3. customto obtain a dark-colored crystalline mass which
  4. customwas recrystallized four times
  5. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-f81ed7746cf54960a82b3160b823f39b
Source dataset
uspto-grants-1976_07
Patent number
US03970622

Reaction notes

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