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

HRID 4034

反応式

HRID 4034 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[N+:18]([O-])=O)[CH2:6][CH2:5]2.[Cl:21]CCl>C(O)C.[Pt]>[ClH:21].[NH2:18][C:12]1[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=1[N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

参加物

5

反応物 2

HCID 6344DichloromethaneHCID 138233414-(5-Bromo-1-indolinyl)-3-nitrotoluene

生成物 1

HCID 138233431-(2-Amino-4-methylphenyl)-5-bromoindoline hydrochloride収率 39%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9a65ccb0ddb418c83d873e96b8bd48d
出典データセット
uspto-grants-1988_02
特許番号
US04723007

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