Stannous chloride dihydrate → 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1597250노트

반응식

HRID 1597250 반응식
C([O:4][CH2:5][CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)(=O)C.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH:13]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:4]

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 21699267HCID 21699267, 화합물

생성물 1

HCID 3163671,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one수율 33%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-(3-nitro-2-pyridyl)ethyl acetate (10.1, 48 mmol), tin(II)chloride dihydrate (54.3 g, 240 mmol) and ethyl acetate was stirred and heated at reflux for 5 hours. The reaction mixture was allowed to cool overnight, filtered through diatomaceous earth and the solvent was removed by evaporation. The resulting oil was purified by flash chromatography using increasingly polar solvent mixtures starting with methylene chloride and ending with methylene chloride/methanol (10/1). Removal of the solvent by evaporation gave 4-azaoxindole (2.1 g, 33%).

후처리

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureto cool overnight
  4. filtrationfiltered through diatomaceous earth
  5. customthe solvent was removed by evaporation
  6. customThe resulting oil was purified by flash chromatography
  7. temperatureusing increasingly polar solvent mixtures
  8. customRemoval of the solvent
  9. customby evaporation

출처 및 근거

ORD 기록
ord-044357275fca4dcfa10416e770fa0fe7
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294532B1

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