反应详情

5,6,7,8-Tetrahydro-3-methylquinoline (6.6 g) was added to o-anisaldehyde (8.16 g) in acetic anhydride (10 ml) and was heated to reflux for 14 hours after which the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (50 ml) and was added to 2N HCl (150 ml), the aqueous layer was basified (Na2CO3) and extracted with ethyl acetate (4×100 ml) dried (MgSO4) and evaporated under reduced pressure. The residue was washed with several aliquots of hot hexane and was then dissolved in a small volume of boiling propan-2-ol and etherial hydrogen chloride was added in excess. On cooling a precipitate formed and was removed by filtration, washed with ether and dried under vacuum to give the title compound as the hydrochloride salt (2.6 g) m.p. 221°-222.5° C.

1. temperaturewas heated
2. temperatureto reflux for 14 hours after which the solvent
3. customwas removed under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
5. additionwas added to 2N HCl (150 ml)
6. extractionextracted with ethyl acetate (4×100 ml)
7. dry with materialdried (MgSO4)
8. customevaporated under reduced pressure
9. washThe residue was washed with several aliquots of hot hexane
10. dissolutionwas then dissolved in a small volume of boiling propan-2-ol and etherial hydrogen chloride
11. additionwas added in excess
12. temperatureOn cooling a precipitate
13. customformed
14. customwas removed by filtration
15. washwashed with ether
16. customdried under vacuum