[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1(=O)[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1>O.O.CC1C=CC(S(O)(=O)=O)=CC=1>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][C:10]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:11]1A mixture of 2-aminobenzonitrile (120 g) and 1,3-cyclohexandione (120 g) in water (400 ml) was heated to 40° and 4-methylbenzenesulfonic acid monohydrate (6.2 g) was added, with stirring. The mixture was stirred at 40° for 1 hr. The mixture was filtered, and the filter cake was washed with water to provide 200 g (93%) of 2-(3-oxocyclohexen-1-yl)aminobenzonitrile, mp 191.4°.
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