反应详情

Phosphorous pentachloride (1.0 g) was added to a stirred solution of 6-acetamido-2-methoxy-8-methylquinoline (1.0 g) in toluene (50 cm3) and the mixture was stirred at 50° for 15 minutes. Acetyl hydrazine (1.35 g) was then added and the mixture was stirred for 3 hours at 60°. The toluene was removed in vacuo, the residue dissolved in ethanol, and aqueous ammonia solution (S.G. 0.88) (25 cm3) was added. Dichloromethane (100 cm3) was added and the organic phase was separated. The aqueous phase was further extracted with dichloromethane (2×25 cm3), and the combined organic phases were dried (MgS04) and evaporated to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 19:1. Combination and evaporation of appropriate fractions afforded 6-[3,5-dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinoline (0.306 g), which was recrystallised from toluene to give microcrystals, m.p. 211°-213° (0.066 g).

1. stirringthe mixture was stirred for 3 hours at 60°
2. customThe toluene was removed in vacuo
3. dissolutionthe residue dissolved in ethanol
4. additionaqueous ammonia solution (S.G. 0.88) (25 cm3) was added
5. additionDichloromethane (100 cm3) was added
6. customthe organic phase was separated
7. extractionThe aqueous phase was further extracted with dichloromethane (2×25 cm3)
8. customthe combined organic phases were dried (MgS04)
9. customevaporated
10. customto give a solid which
11. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
12. washeluting with dichloromethane
13. customCombination and evaporation of appropriate fractions