Stannous chloride dihydrate → Ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate

HRID 565061ノート

反応式

HRID 565061 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:6]2[CH3:21].O.O.[Sn](Cl)Cl.O.N>C(O)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[C:7]=2[N:6]([CH3:21])[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4]3)=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 61436Stannous chloride dihydrateHCID 12896473Azane;hydrateHCID 21194161HCID 21194161、化合物

生成物 1

HCID 21194433Ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate収率 71.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4.10 g (10.9 mmol) of ethyl 4-chloro-1-methyl-7-(4-nitrophenoxy)-2-indolecarboxylate, 12.34 g (54.7 mmol) of tin (II) chloride dihydrate and 150 ml of ethanol was stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature, 28% ammonia water was added to render alkaline and the mixture was extracted with ethyl acetate. Insoluble matters were filtered off. The filtrate was washed with 5% sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2.70 g of ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. filtrationInsoluble matters were filtered off
  4. washThe filtrate was washed with 5% sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e8598d7f8f0a453aae2910b5a19101a7
出典データセット
uspto-grants-2001_01
特許番号
US06169107A

反応ノート

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