Diethyl Ether → 5-Chloro-1,3-dihydro-3-hydroxy-3-(2-methylphenyl)indol-2-one

HRID 234481노트

반응식

HRID 234481 반응식
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].CCOCC.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2=[O:26]>O.C1COCC1>[CH3:19][C:18]1[CH:22]=[CH:23][CH:24]=[CH:16][C:17]=1[Mg:1][Br:2].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[C:19]2([OH:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9]

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 72362-BromotolueneHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium2회

생성물 2

HCID 190764695-Chloro-1,3-dihydro-3-hydroxy-3-(2-methylphenyl)indol-2-one수율 126.4%HCID 178424303HCID 178424303, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-methylphenylmagnesium bromide is prepared from 2.7 g of magnesium, 19 g of 1-bromo-2-methylbenzene and 100 ml of ether. A mixture of 5.04 g of 5-chloroisatin and 100 ml of THF is cooled in an ice bath under an argon atmosphere and the solution of magnesium compound prepared above is added slowly. After stirring for 4 hours, water is added and the solvents are evaporated off under vacuum. The residue is extracted with AcOEt, the precipitate formed is filtered off and the organic phase of the filtrate is dried over magnesium sulfate and evaporated under vacuum. The residue obtained, combined with the precipitate previously filtered off, is crystallized from MeOH to give 4.8 g of the expected product.

후처리

  1. temperatureis cooled in an ice bath under an argon atmosphere
  2. additionabove is added slowly
  3. customthe solvents are evaporated off under vacuum
  4. extractionThe residue is extracted with AcOEt
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. dry with materialthe organic phase of the filtrate is dried over magnesium sulfate
  8. customevaporated under vacuum
  9. customThe residue obtained
  10. filtrationpreviously filtered off
  11. customis crystallized from MeOH

출처 및 근거

ORD 기록
ord-e1ae98286b044cde9273620f49baa006
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594023

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