Sodium ethoxide → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=1.C([O-])C.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1Participants
3
Procedure
3.0 g (8.59 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-phenyl]acetamide (example 3, intermediate 5) were heated to reflux in 100 ml of 21% strength sodium ethanolate solution. Solid sodium ethanolate was added depending on the progress of the reaction, until complete conversion was achieved. For workup, the solvent was removed and the residue was taken up in H2O. It was extracted twice with dichloromethane. The combined organic phases were dried with MgSO4 and concentrated. Further purification takes place by chromatography on silica gel with an ethyl acetate/heptane mixture, resulting in the aniline compound as a yellow oil.