反应详情

A solution of 15 g. of 4-methylaminocyclohexanone and 18.4 g. of 3-methylhydrazine hydrochloride in 200 ml. of absolute ethyl alcohol and 50 ml. of 4-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for six hours, cooled, and filtered to give 12.3 g. of solids which were slurried in 50 ml. of water. The slurry was cooled, the solids were collected by filtration, suspended in ether-chloroform, and the suspension was treated with dilute potassium hydroxide. The ether-chloroform extract was evaporated to dryness under reduced pressure to give 7.6 g. of 3-(methylamino)-7-methyl-1,2,3,4-tetrahydrocarbazole, m.p. 163°-166° C. The alcoholic reaction mixture filtrate was evaporated to dryness under reduced pressure, the residue was boiled in isopropyl alcohol, and the insoluble material was collected by filtration, dissolved in water and the resulting solution was made alkaline with dilute potassium hydroxide. The resulting solids were collected by filtration to give, after recrystallization from ethyl acetate, 3.6 g. of 3-(methylamino)-5-methyl-1,2,3,4-tetrahydrocarbazole, m.p. 187°-190° C., which contained about 6% of the 7-methyl isomer as determined by gas chromatographic analysis.

1. temperatureunder reflux for six hours
2. temperaturecooled
3. filtrationfiltered
4. customto give 12.3 g
5. temperatureThe slurry was cooled
6. filtrationthe solids were collected by filtration
7. additionthe suspension was treated with dilute potassium hydroxide
8. extractionThe ether-chloroform extract
9. customwas evaporated to dryness under reduced pressure
10. customto give 7.6 g
11. customThe alcoholic reaction mixture filtrate was evaporated to dryness under reduced pressure
12. filtrationthe insoluble material was collected by filtration
13. dissolutiondissolved in water
14. filtrationThe resulting solids were collected by filtration
15. customto give
16. customafter recrystallization from ethyl acetate, 3.6 g