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

HRID 1597250Notes

Reaction equation

HRID 1597250 reaction equation
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]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21699267HCID 21699267, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-044357275fca4dcfa10416e770fa0fe7
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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