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

HRID 965529ノート

反応式

HRID 965529 の反応式
[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]

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 72362-BromotolueneHCID 872035-chloro-1H-indole-2,3-dioneHCID 5462224Magnesium2 回

生成物 2

HCID 190764695-Chloro-1,3-dihydro-3-hydroxy-3-(2-methylphenyl)indol-2-one収率 126.4%HCID 178424303HCID 178424303、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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. M.p.=285°-295° C.

後処理

  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

出典と根拠

ORDレコード
ord-e9214d8a75b34e7da2f07c5147155698
出典データセット
uspto-grants-1998_06
特許番号
US05773612

反応ノート

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