Isatin → 1-(4-Methoxyphenyl)indoline-2,3-dione

HRID 11199

반응식

HRID 11199 반응식
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])=[CH:16][CH:17]=1

참가 물질

7

반응물 3

HCID 7054IsatinHCID 77304-BromoanisoleHCID 24758Sodium hydride

생성물 1

HCID 139250941-(4-Methoxyphenyl)indoline-2,3-dione

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of isatin (2.5 g, 0.017 mol) in anhydrous DMF (50 ml) was cooled to 0° C. under a nitrogen atmosphere and treated with sodium hydride (0.5 g, 1.2 equivalents). A purple solution was formed which was stirred at 0° C. for 30 minutes and then warmed to room temperature. 4-Bromoanisole (2.13 ml, 1 equivalent) was added followed by copper iodide (6.46 g, 2 equivalents). The reaction was heated in an oil-bath at 145° C. for 7 hours. The reaction was then cooled to room temperature and diluted with an equal volume of ethyl acetate. This suspension was filtered and the filtrate was evaporated to dryness. TLC (1:4, ethyl acetate:hexanes) indicated a very clean reaction; Rf (product)=0.5. The crude material was used as such for the next reaction.

후처리

  1. customA purple solution was formed which
  2. temperaturewarmed to room temperature
  3. temperatureThe reaction was heated in an oil-bath at 145° C. for 7 hours
  4. temperatureThe reaction was then cooled to room temperature
  5. filtrationThis suspension was filtered
  6. customthe filtrate was evaporated to dryness
  7. customa very clean reaction
  8. customsuch for the next reaction

출처 및 근거

ORD 기록
ord-e59131b79bd04d71ba5590af6c25b9b8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07097995B2

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