Ammonia → 4-(Aminomethyl)-3,5-difluorobenzonitrile
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:13])[C:9]=1[CH:10]=[N:11]O)[C:5]#[N:6].N>C(O)(=O)C.[Zn]>[NH2:11][CH2:10][C:9]1[C:8]([F:13])=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
An excess of zinc powder was added to a stirred mixture of 3,5-difluoro-4-((hydroxyimino)methyl)benzonitrile (130 mg, 0.7 mmol) in acetic acid (10 mL) then heated to 60° C. for 2 h. The mixture was made basic by addition of aqueous ammonia and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to afford 4-(aminomethyl)-3,5-difluorobenzonitrile (100 mg, 0.6 mmol) as a colourless oil.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cefa60c2245a4bb4b9e843756c5f2c0c
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296725B2
Reaction notes
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