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

HRID 34318

반응식

HRID 34318 반응식
[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.CC1C=CC2N=C(N3CCN(C)CC3)C3C=CC=C4CCN(C=34)C=2C=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

참가 물질

6

반응물 3

HCID 241BenzeneHCID 138233265-Chloro-1-(4-chloro-2-nitrophenyl)indolineHCID 2129924710-Methyl-6-(4-methyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

생성물 1

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

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 702Ethanol용매

실험 절차

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-4-chlorophenyl)-5-chloroindoline hydrochloride ethanolate in 58% overall yield, m.p. 177°-180° C.

후처리

  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)

출처 및 근거

ORD 기록
ord-58674ca66eff49ce9bb2d059a297f1ae
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761411

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