Ammonia → 3-Amino-2-methylbenzonitrile
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Cl[C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10]([Cu])#[N:11].N.O=O>CN1CCCC1=O.Cl[Cu].O>[NH2:5][C:4]1[C:3]([CH3:9])=[C:2]([CH:8]=[CH:7][CH:6]=1)[C:10]#[N:11]Cl[C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10]([Cu])#[N:11].N.O=O>CN1CCCC1=O.Cl[Cu].O>[NH2:5][C:4]1[C:3]([CH3:9])=[C:2]([CH:8]=[CH:7][CH:6]=1)[C:10]#[N:11]283 g (2.0 mol) of 3-chloro-2-methylaniline are dissolved in 250 ml of N-methylpyrrolidone and admixed with 200 g (2.23 mol) of CuCN. The reaction mixture is subsequently stirred under N2 and at 225° C. for six hours. After cooling to 100° C., the reaction mixture is poured into 2.5 l of 25 percent ammonia solution and stirred at 25° C. for one hour. During this time, the atmospheric oxygen oxidizes the Cu(I) nitrile complex of the product to a water-soluble Cu(II) salt, which is evident by the formation of the intensively blue tetramine complex. Some of the CuCl remains undissolved as a white solid and can be easily removed by filtration with suction. The filtrate is extracted with approximately 2 l of methyl tert-butyl ether and then washed with ammonia water and finally three times with water. The organic phase is dried over sodium sulfate and concentrated, affording 255 g (89% yield of crude product) of a dark oil which can be purified by recrystallization from cyclohexane/toluene (5:1).
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