Water → HCID 4448611, 화합물

HRID 635259노트

반응식

HRID 635259 반응식
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[CH:21]=[CH:22][C:23](Cl)=[O:24].O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[O:24])[CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 10328IndolineHCID 53411290HCID 53411290, 화합물

생성물 1

HCID 4448611HCID 4448611, 화합물수율 86.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
5 °C

실험 절차

Triethylamine (9.2 ml) was added at room temperature to a solution of indoline (20 g) in DCM (200 ml) and the mixture was cooled till 5° C. A solution of m-chloro-cinnamoyl chloride (40 g) in DCM (100 ml) was added dropwise and the mixture was stirred at room temperature for 48 hours. Water was added, the organic layer was decanted, washed with water, dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10), yielding 41 g (73%) of 1-[3-(3-chlorophenyl)-1-oxo-2-propenyl]-2,3-dihydro-1H-indole (interm. 37).

후처리

  1. customthe organic layer was decanted
  2. washwashed with water
  3. customdried
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10)

출처 및 근거

ORD 기록
ord-28287d05088a435da52add8df74eaf92
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187786B1

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