反应详情

3.0 g (8.6 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-acetamide (example 1) was dissolved in 100 ml of 20% strength sodium ethanolate solution and heated under reflux for four hours. A further 2.0 g (29.4 mmol) of solid sodium ethanolate was added, and the mixture was heated under reflux for three more 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. Further purification by chromatography on silica gel (ethyl acetate/heptane 1:1) resulted in the aniline as a yellowish oil in quantitative yield.

1. temperatureheated
2. temperatureunder reflux for four hours
3. temperaturethe mixture was heated
4. temperatureunder reflux for three more hours
5. customFor workup, the solvent was removed in vacuo
6. extractionextracted twice with dichloromethane
7. dry with materialThe combined organic phases were dried with MgSO4
8. concentrationconcentrated
9. customFurther purification by chromatography on silica gel (ethyl acetate/heptane 1:1)