Hydrochloric Acid → Indol-2-one

HRID 648694

反応式

HRID 648694 の反応式
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

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetateHCID 13755074HCID 13755074、化合物

生成物 1

HCID 17904787Indol-2-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
-65 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5e44192c0064fa9a8d5a7f3ff3b3a1c
出典データセット
uspto-grants-1988_04
特許番号
US04736034

関連ノート

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