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

HRID 1722273Notes

Reaction equation

HRID 1722273 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]>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

4

Reactant 1

HCID 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 filtered. 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. filtrationfiltered
  2. additionTo the filtrate is added water
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-c8a7685be8ea415ba97cc65b52bf4556
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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