Hydrochloric Acid → Indol-2-one

HRID 2309187ノート

反応式

HRID 2309187 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 137550743-(3-Amino-4-methoxyphenyl)-1-trifluoroacetyl piperidine

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 2 N 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-25ba4f0be8b149e9bc08b532dd6608ca
出典データセット
uspto-grants-1987_09
特許番号
US04694011

反応ノート

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