反应详情

A solution of 2-ethyl-4-[(2'-(2-tributylstannyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline in toluene (15 ml), prepared in situ by refluxing for 90 hours a mixture of 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carbonitrile (0.9 g) and a solution of tributyltin azide in toluene (15 ml) [the latter prepared by reaction of tributyltin chloride (3.3 g) and sodium azide (1.13 g) in water (22.5 ml) at ambient temperature for 4 hours, followed by extraction with toluene and azeotropic removal of water from the extract to leave a volume of 15 ml], was added slowly over 1 hour to a solution of sodium nitrite (2.5 g) in water (10 ml) containing 12% w/v hydrochloric acid (10 ml), maintaining the temperature of the mixture below 5° C. A solution of sulphamic acid (1.43g) in water (10ml) was then added, maintaining the temperature below 5° C., and the mixture stirred for 1 hour. The resultant suspended semi-solid was collected by filtration and washed with water (3×10 ml), followed by toluene (10 ml). The semi-solid was then added to tetrahydrofuran (THF) (40 ml), which caused the product to dissolve and then crystallise as a white solid. After cooling for one hour the solid was collected by filtration, washed with THF (5 ml) and dried to give 2-ethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline hydrochloride; m.p. 179°-180° C. (dec.); NMR (d6 -DMSO): 1.46(t, 3H), 3.18(q,2H), 5.68(s,2H), 7.22(d,2H), 7.5-7.8(m,7H), 7.83(t,1H), 8.08(t,1H), 8.18(d,1H), 8.32(d,1H).

1. temperatureby refluxing for 90 hours
2. extractionfollowed by extraction with toluene and azeotropic removal of water from the
3. extractionextract
4. customto leave a volume of 15 ml],
5. additioncontaining 12%
6. temperaturemaintaining the temperature of the mixture below 5° C
7. temperaturemaintaining the temperature below 5° C.
8. filtrationwas collected by filtration
9. washwashed with water (3×10 ml)
10. additionThe semi-solid was then added to tetrahydrofuran (THF) (40 ml), which
11. dissolutionto dissolve
12. customcrystallise as a white solid
13. temperatureAfter cooling for one hour the solid
14. filtrationwas collected by filtration
15. washwashed with THF (5 ml)
16. customdried