Water → 3,4-Dihydroisoquinolin-7-amine
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[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.O.[OH-].[K+]>C(O)C.Cl>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.O.[OH-].[K+]>C(O)C.Cl>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1
7-Nitro-3,4-dihydroisoquinoline (0.60 g, 3.4 mmol) [prepared according to the procedure of A. P. Venkov et al, Syn. Commun., 1996 26 127] was dissolved in ethanol (100 ml) and heated to 60° C. This hot solution was treated with a solution of tin (II) chloride dihydrate (3.08 g, 13.7 mmol) in conc. HCl (10 ml). The resultant mixture was heated at 60° for 1 h. Upon cooling, the reaction mixture was poured into water (100 ml) and basified (pH 9) with KOH pellets, liberating an oily residue. This residue was extracted into dichloromethane and dried over magnesium sulfate. Purification by chromatography through silica gel, eluting with (0.5% conc. ammonia: 4.5% methanol: 95% dichloromethane) yielded the title compound as a dark yellow oil (0.44 g, 88%).
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