Ammonia → 4-Amino-3-methylbenzonitrile
Reaction equation
C[N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.BrC1C=C[C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1.[Cu](C#N)C#N.N>O>[NH2:13][C:12]1[CH:3]=[CH:4][C:5]([C:6]#[N:2])=[CH:10][C:11]=1[CH3:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
To an N-methylpyrrolidone (0.5 L) solution of 4-bromo-2-methylaniline (40 g) was added copper cyanide (38.5 g). The stirred mixture was heated at 200° C. for 2.5 hrs. The mixture was cooled to room temperature then water (1.9 L) and ammonia (0.5 L, 32%) were added. The mixture was extracted with ethyl acetate (2×1.2 L) and the combined organic phases then washed with a mixture of water/ammonia (0.5 L+0.2 L, 32%) and dried over Na2SO4. The solvent was evaporated under vacuum to give the title compound as a brown solid (27.5 g). This material was used in the next step without further purification.
Workup
- temperatureThe mixture was cooled to room temperature
- extractionThe mixture was extracted with ethyl acetate (2×1.2 L)
- washthe combined organic phases then washed with a mixture of water/ammonia (0.5 L+0.2 L, 32%)
- dry with materialdried over Na2SO4
- customThe solvent was evaporated under vacuum
Sources & evidence
- ORD record
- ord-c19abb890ba942b1bdac02504a3746b0
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933132B2
Reaction notes
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