Dimethylformamide → methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate

HRID 55472

反応式

HRID 55472 の反応式
[CH3:1]I.N1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)CC1C(O)=O.[CH3:15][N:16]([CH3:19])[CH:17]=O.[C:20](=[O:23])([O-])[O-:21].[K+].[K+]>O>[CH3:15][N:16]1[C:19]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:6][CH:17]1[C:20]([O:21][CH3:1])=[O:23]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86074Indoline-2-carboxylic acid

生成物 1

HCID 12658762methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

11.7 ml of methyl iodide were added dropwise to a mixture of 10.3 g of (±)-indoline-2-carboxylic acid, 200 ml of dimethylformamide and 25.4 g of anhydrous potassium carbonate, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 7:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 9.12 g of the title compound having Rf=0.77 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

後処理

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-966454dd359340f6973c8bd716fa99f3
出典データセット
uspto-grants-1997_04
特許番号
US05624935

関連ノート

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