반응 #4188

반응 방정식

4-(5-bromo-1-indolinyl)-3-nitrotoluene

dichloromethane

→

product

수율 39.0%

1-(2-Amino-4-methylphenyl)-5-bromoindoline hydrochloride

수율 39.0%

용매

ethanol

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   농축concentrated
3. 3
   기타The residue was dried under vacuum at 55° C
4. 4
   기타Purification
5. 5
   세척eluted with a mixture of hexane:dichloromethane (3:1, 2 l and 1:1, 1 l)
6. 6
   workup.ADDITIONThe fractions containing pure product
7. 7
   농축concentrated
8. 8
   workup.DISSOLUTIONThe residue was dissolved in ether (250 ml)
9. 9
   workup.ADDITIONadded to a methanol/hydrogen chloride solution
10. 10
    workup.STIRRINGthe mixture was stirred at 0° C. for 10 minutes
11. 11
    여과The precipitate was filtered
12. 12
    기타dried

실험 절차

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.

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