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

HRID 1597250ノート

反応式

HRID 1597250 の反応式
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]

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 21699267HCID 21699267、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-044357275fca4dcfa10416e770fa0fe7
出典データセット
uspto-grants-2001_09
特許番号
US06294532B1

反応ノート

読み込み中…