Water → 1-(4-Isopropylphenyl)-1H-indole-2-carboxylic acid

HRID 505629

반응식

HRID 505629 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].Br[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.[Cu]=O>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([OH:12])=[O:11])=[CH:15][CH:16]=1)([CH3:22])[CH3:21]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 114621-Bromo-4-isopropylbenzeneHCID 72899Indole-2-carboxylic acid

생성물 1

HCID 686999491-(4-Isopropylphenyl)-1H-indole-2-carboxylic acid

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 6228Dimethylformamide용매

실험 절차

A suspension of 128.8 g (0.8 mol) of 1H-indole-2-carboxylic acid, of 159.2 g (0.8 mol) of 4-bromocumene, of 111.6 g (0.808 mol) of potassium carbonate and of 8 g (0.1 mol) of copper oxide in 200 ml of dimethylformamide is stirred at reflux for 24 hours. After cooling, 6 l of water are added to the beige suspension obtained. The suspension is filtered and then the insoluble material is taken up in 1 l of a 5N hydrochloric acid solution. This mixture is extracted with 500 ml of dichloromethane. The organic phase is washed with water, dried over sodium sulfate and then concentrated under reduced pressure. After drying under reduced pressure, 204.4 g of a white solid are obtained, which solid is used as is in the following stage.

후처리

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. customobtained
  4. filtrationThe suspension is filtered
  5. extractionThis mixture is extracted with 500 ml of dichloromethane
  6. washThe organic phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dry with materialAfter drying under reduced pressure, 204.4 g of a white solid
  10. customare obtained

출처 및 근거

ORD 기록
ord-b0ac66fbb2b44ca2b9080c8084e9d25d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781477B2

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