反应详情

Sodium borohydride (1.19 g) in ethanol was added dropwise to ethyl N-(3,4-dichlorobenzyl)-5-nitroindole-2-carboxylate (12.4 g) and stannous chloride dihydrate (35.6 g) in ethanol at 60° C. and reaction stirred for 5 hours. The mixture was then cooled, made basic with 2N sodium hydroxide and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated to give an oil which crystallised upon trituration with i-hexane. Filtration yielded the desired end product as a pale brown solid (1.18 g, 10%); NMR δ (CDCl3) 1.32 (t, 3H), 4.26 (q, 2H), 6.69 (s, 2H), 6.78-7.35 (m, 7H); M/z (−) 363 (M+), 274, 267, 265, 151, 121, 102.

1. customreaction
2. temperatureThe mixture was then cooled
3. extractionextracted with ethyl acetate
4. dry with materialCombined organic extracts were dried (MgSO4)
5. concentrationconcentrated
6. customto give an oil which
7. customcrystallised upon trituration with i-hexane
8. filtrationFiltration