Water → 2-Amino-4,5-difluoro-3-methylbenzonitrile

HRID 2351889Notes

Reaction equation

HRID 2351889 reaction equation
[NH2:1][C:2]1[C:9]([CH2:10]SC)=[C:8]([F:13])[C:7]([F:14])=[CH:6][C:3]=1[C:4]#[N:5].O>C(O)C.[Ni]>[NH2:1][C:2]1[C:9]([CH3:10])=[C:8]([F:13])[C:7]([F:14])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 962WaterHCID 156318212-Amino-4,5-difluoro-3-methylthiomethylbenzonitrile

Product 1

HCID 156318222-Amino-4,5-difluoro-3-methylbenzonitrileYield 76.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 2-amino-4,5-difluoro-3-methylthiomethylbenzonitrile (4.0 g) in ethanol (80 ml) are added Raney nickel (40 ml) with ethanol (80 ml). The mixture is stirred at 40°-50° C. for 30 minutes, and then filterd. To the filtrate is added water, the reaction mixture is extracted with ethyl acetate. The extract is dried over magnesium sulfate and concentrated. The product is recrystallized from n-hexane to give 2-amino-4,5-difluoro-3-methylbenzonitrile (2.4 g), as a white crystal, m.p. 114°-116° C.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. dry with materialThe extract is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-61ee275e159d4d59840d1550833caa4e
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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