反应详情

A mixture of methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate (25 g., 0.13 m), formamide (11.6, 0.26 m) and sodium methoxide (from 2.99 g., 0.13 m sodium) was heated with stirring in an oil bath at 120° from 1 hour. The reaction mixture was further heated at 100° for 3 hours under reduced pressure (15 mm Hg). The cooled reaction mixture was diluted with 2N HCl to give an acidic solution which was extracted with ethyl acetate (2× 50 ml.) and the combined extracts discarded. The aqueous solution was adjusted to pH 9.0 with solid Na2CO3, saturated with NaCl and extracted with chloroform (3× 100 ml.). The combined extracts were dried and evaporated to give a pale yellow oil which solidified on trituration with n-hexane. Recrystallisation from ethyl acetate gave the title compound as colourless cubes (18.6 g., 88%) m.p. 110°. Found: C, 69.6; H, 7.4; N, 14.4%. C11H14N2O requires: C, 69.5; H, 7.4; N, 14.7%.

1. temperaturewas heated
2. temperatureThe reaction mixture was further heated at 100° for 3 hours under reduced pressure (15 mm Hg)
3. customThe cooled reaction mixture
4. customto give an acidic solution which
5. extractionwas extracted with ethyl acetate (2× 50 ml.)
6. extractionextracted with chloroform (3× 100 ml.)
7. customThe combined extracts were dried
8. customevaporated
9. customto give a pale yellow oil which
10. customRecrystallisation from ethyl acetate