Ammonia → 4-(Aminomethyl)-3-chlorobenzonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[Cl:11].[NH3:12].Cl>CO>[NH2:12][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[Cl:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 18 °C
Procedure
To a mixture of 4-(bromomethyl)-3-chlorobenzonitrile (11 g, 49 mmol, 1.0 equiv) and 6 M NH3 in methanol (200 mL) was stirred at 18° C. for 17 h. Aqueous HCl (1 M, 200 mL) was added, and the water layer was washed with ethyl acetate. The aqueous phase was adjusted to pH 9-10 with 1 M NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried with magnesium sulfate, and concentrated. The residue was purified on silica gel to afford 2.71 g of the title compound. MS (ES+): m/e 167.0 [M+H]+.
Workup
- washthe water layer was washed with ethyl acetate
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried with magnesium sulfate
- concentrationconcentrated
- customThe residue was purified on silica gel
Sources & evidence
- ORD record
- ord-f3568bc6881948a39ea924dc90520270
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173805B2
Reaction notes
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