Hydrochloric Acid → Indol-2-one

HRID 648694

반응식

HRID 648694 반응식
N[C:2]1[CH:3]=[C:4]([CH:10]2CCC[N:12](C(=O)C(F)(F)F)[CH2:11]2)[CH:5]=[CH:6][C:7]=1OC.CCC([O:26]CC)=S.ClOC(C)(C)C.Cl>C(N(CC)CC)C.C(Cl)Cl>[N:12]1[C:11](=[O:26])[CH:10]=[C:4]2[C:5]=1[CH:6]=[CH:7][CH:2]=[CH:3]2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetateHCID 13755074HCID 13755074, 화합물

생성물 1

HCID 17904787Indol-2-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
-65 °C

실험 절차

604 mg of 3-(3-amino-4-methoxyphenyl)-1-trifluoroacetyl piperidine were added with stirring under an inert atmosphere to 20 ml of methylene chloride and 0.26 ml of ethyl methylthioacetate cooled to -65° C., and then 0.24 ml of tert-butyl hypochlorite were added over 5 minutes. After stirring for an hour, 0.29 ml of triethylamine were added dropwise and the temperature was allowed to return to ambient. 5 ml of aqueous 2N hydrochloric acid were added and the mixture was stirred for an hour. The decanted organic phases were washed with water, dried and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica (eluent benzene--ethyl acetate 7-3) to obtain 580 mg of 1,3-dihydro-7-methoxy-3-methylthio-4-[1-trifluoroacetyl)-3-piperidinyl]-2H-indol-2-one which after crystallization from ethanol melted at ≈189° C.

후처리

  1. stirringthe mixture was stirred for an hour
  2. washThe decanted organic phases were washed with water
  3. customdried
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was chromatographed over silica (eluent benzene--ethyl acetate 7-3)

출처 및 근거

ORD 기록
ord-b5e44192c0064fa9a8d5a7f3ff3b3a1c
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04736034

연결된 노트

불러오는 중…