Benzene → 1-(2-Amino-4-chlorophenyl)-5-chloroindoline hydrochloride ethanolate

HRID 34350

反応式

HRID 34350 の反応式
[Cl: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]([Cl:17])=[CH:13][C:12]=1[N+:18]([O-])=[O:19])[CH2:6][CH2:5]2.[CH:21]1[CH:26]=CC=CC=1>[Pt].C(O)C>[CH2:26]([O-:19])[CH3:21].[ClH:1].[NH2:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

参加物

5

反応物 2

HCID 241BenzeneHCID 138233265-Chloro-1-(4-chloro-2-nitrophenyl)indoline

生成物 1

HCID 867414801-(2-Amino-4-chlorophenyl)-5-chloroindoline hydrochloride ethanolate

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 702Ethanol溶媒

実験手順

A Parr bottle, charged with 12.4 g (0.040 mole) of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline of Example 8a, 100 ml of benzene, 100 ml of absolute ethanol and 0.5 g of 1% Pt/C was shaken under an initial hydrogen pressure of 57 psig until uptake ceased. The catalyst was then removed by filtration and the filtrate was concentrated in vacuo to an oil weighing 11.2 g (100%). This was dissolved in 30 ml of ethanol and then 30 ml of ether saturated with hydrogen chloride was added. An additional 500 ml of plain ether was added, and the mixture was stirred at 0° C., to maximize precipitation. The hydrochloride salt was collected, dried, and found to weigh 9.2 g (73%), m.p. 174°-178° C. Recrystallization from ethanol (charcoal) afforded 1-(2-amino-4chlorophenyl)-5-chloroindoline hydrochloride ethanolate in 58% overall yield, m.p. 177°-180° C.

後処理

  1. customThe catalyst was then removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo to an oil
  3. dissolutionThis was dissolved in 30 ml of ethanol
  4. addition30 ml of ether saturated with hydrogen chloride was added
  5. additionAn additional 500 ml of plain ether was added
  6. stirringthe mixture was stirred at 0° C.
  7. customprecipitation
  8. customThe hydrochloride salt was collected
  9. customdried
  10. customRecrystallization from ethanol (charcoal)

出典と根拠

ORDレコード
ord-af432a9176064d2d9012f4cb7f5d8f8a
出典データセット
uspto-grants-1988_08
特許番号
US04761412

関連ノート

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