Hydrochloric Acid → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 366564노트

반응식

HRID 366564 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:15][CH2:16][C:17](Cl)=[O:18].Cl>ClC(Cl)C.C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)=[O:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one수율 98%

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

2-Oxindole (6.7 g) was added to a stirred suspension of 23 g of aluminum chloride in 30 mL of dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed at 40 to 50° C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-dec44caaeee243b2bc7f5e3de4486466
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130238

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