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

HRID 565061노트

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HRID 565061 반응식
[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

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 12896473Azane;hydrateHCID 21194161HCID 21194161, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8598d7f8f0a453aae2910b5a19101a7
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169107A

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