反应详情

Sodium hydride (50% dispersion in oil; 0.2 g) was added to a stirred suspension of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (1.0 g) in DMF (10 ml) under an atmosphere of argon. The mixture was stirred until effervescence ceased and 4-nitrobenzyl bromide (1.1 g) was added. The mixture was then stirred for 16 hours. The mixture was then poured into water (50 ml) and extracted twice with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried (MgSO4) and solvent was removed by evaporation to give an oil. The oil was purified by flash chromatography, eluting with ethyl acetate/dichloromethane (1:4 v/v) to give 5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one (B) as a solid (1.03 g); m.p. 105°-106° C.; NMR (CDCl3): 1.22(t, 3H), 1.36(t, 3H), 2.77(q, 2H), 3.11(q, 2H), 5.57(s, 2H), 6.69(s, 1H), 6.77(d, 1H), 7.38(d, 2H), 8.03(d, 1H), 8.19(d, 2H); mass spectrum (CI, ammonia): 338 (M+H)+ ; microanalysis, found: C, 67.0; H, 5.7; N, 12.4%; C19H19N3O3 requires: C, 67.6; H, 5.7; N, 12.5%.

1. stirringThe mixture was then stirred for 16 hours
2. extractionextracted twice with ethyl acetate
3. washThe combined extracts were washed with saturated sodium chloride solution
4. dry with materialdried (MgSO4) and solvent
5. customwas removed by evaporation
6. customto give an oil
7. customThe oil was purified by flash chromatography
8. washeluting with ethyl acetate/dichloromethane (1:4 v/v)