[CH3:1][C:2]1([CH3:23])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[NH:4][CH:3]1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1>C(O)C.Cl.[Fe]>[NH2:20][C:16]1[CH:15]=[C:14]([CH:3]2[C:2]([CH3:1])([CH3:23])[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=3)[NH:4]2)[CH:19]=[CH:18][CH:17]=1To a mixture of 3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (4 g, 13 mmol) in ethanol 95% (150 mL) and 10% hydrochloric acid (10 mL) was added iron (2.18 g, 39.2 mmol). The reaction mixture was stirred at 95° C. for 6 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with 30% sodium hydroxide in water (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3-amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (0.9 g, 25%) as a yellow solid: LC/MS m/e calcd for C18H19N3 (M+H)+: 278.37, observed: 278.1.
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