N-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)acetamide → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

Participants

Reaction Steps

3.0 g (8.6 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]acetamide (intermediate 5) were dissolved in 100 ml of 20% sodium ethoxide solution and heated to reflux for 4 hours. A further 2.0 g (29.4 mmol) of solid sodium ethoxide were added and the mixture was heated to reflux for another 3 hours. For workup, the solvent was removed in vacuo, and the residue was taken up in 200 ml of H2O and extracted twice with dichloromethane. The combined organic phases were dried with MgSO4 and concentrated. For further purification, chromatography was effected on silica gel (1:1 ethyl acetate/heptane) to obtain the aniline as a yellowish oil in quantitative yield.

Provenance & Evidence