反应详情

A mixture of 20 g (0.084 mole) of 5-hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine, 10 g of 10% palladium on carbon, 2.3 g of para-toluenesulfonic acid and 200 ml of cumene was heated at its reflux temperature for 24 hours. The mixture was filtered hot, and then the filtrate was evaporated to provide a residue. This residue was dissolved in dilute hydrochloric acid. This solution was extracted with diethyl ether and the acid layer was then neutralized with 50% aqueous sodium hydroxide solution. The product was extracted into diethyl ether. The organic layer was dried and then evaporated to provide a solid residue. Recrystallization from methanol provided white crystals of 5-phenylquinaldine. Analysis: Calculated for C16H13N.H2O: %C, 81.0; %H, 6.4; %N, 5.8; Found: %C, 81.4; %H, 6.6; %N, 5.5. The structure assignment was confirmed by nuclear magnetic resonance spectral analysis.

1. temperaturewas heated at its
2. temperaturereflux temperature for 24 hours
3. filtrationThe mixture was filtered hot
4. customthe filtrate was evaporated
5. customto provide a residue
6. extractionThis solution was extracted with diethyl ether
7. extractionThe product was extracted into diethyl ether
8. customThe organic layer was dried
9. customevaporated
10. customto provide a solid residue
11. customRecrystallization from methanol provided white crystals of 5-phenylquinaldine