反应详情

To a warm solution of 4-(5-bromo-1-indolinyl)-3-nitrotoluene (10 g, 0.03 mole) in dichloromethane (40 ml) and ethanol (160 ml) was added 1% platinum-on-carbon (2.0 gm). The mixture was shaken under hydrogen (57 psi) for 3.5 hours. The mixture was filtered and concentrated. The residue was dried under vacuum at 55° C. Purification was accomplished by flash chromatography over silica gel (100 g), eluted with a mixture of hexane:dichloromethane (3:1, 2 l and 1:1, 1 l). The fractions containing pure product were pooled and concentrated. The residue was dissolved in ether (250 ml) and added to a methanol/hydrogen chloride solution, and the mixture was stirred at 0° C. for 10 minutes. The precipitate was filtered and dried to afford 4.0 g (39%) of product, mp 195°-200° C. dec.

1. filtrationThe mixture was filtered
2. concentrationconcentrated
3. customThe residue was dried under vacuum at 55° C
4. customPurification
5. washeluted with a mixture of hexane:dichloromethane (3:1, 2 l and 1:1, 1 l)
6. additionThe fractions containing pure product
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in ether (250 ml)
9. additionadded to a methanol/hydrogen chloride solution
10. stirringthe mixture was stirred at 0° C. for 10 minutes
11. filtrationThe precipitate was filtered
12. customdried