反应详情

The N-oxide (60 g.) was dissolved in acetic anhydride (120 ml.) and added to boiling acetic anhydride (120 ml.) and the mixture heated at reflux for 30 minutes. The solvent was removed in vacuo and the residual oil was treated with 10% hydrochloric acid (700 ml.) and the solution heated on a steam bath for 2 hours. The cooled reaction mixture was adjusted to pH 9.0 with sodium hydroxide and extracted with ether (3 × 100 ml). The combined ethereal extracts were washed with saturated brine, dried (MgSO4) and the solvent removed in vacuo. The resultant oil as distilled at 0.15 mmHg to give a colourless oil (22 g.) b.p. 70°-78° C which crystallised from n-hexane to give 8-hydroxy-3-methyl-5,6,7,8-tetrahydroquinoline as colourless needles m.p. 58° C.

1. additionadded
2. temperaturethe mixture heated
3. temperatureat reflux for 30 minutes
4. customThe solvent was removed in vacuo
5. additionthe residual oil was treated with 10% hydrochloric acid (700 ml.)
6. temperaturethe solution heated on a steam bath for 2 hours
7. customThe cooled reaction mixture
8. extractionextracted with ether (3 × 100 ml)
9. washThe combined ethereal extracts were washed with saturated brine
10. dry with materialdried (MgSO4)
11. customthe solvent removed in vacuo
12. distillationThe resultant oil as distilled at 0.15 mmHg
13. customto give a colourless oil (22 g.) b.p. 70°-78° C which
14. customcrystallised from n-hexane