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

HRID 131642

反応式

HRID 131642 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-668e467e54394f739aaca9fced868beb
出典データセット
uspto-grants-2008_06
特許番号
US07384969B2

関連ノート

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