Sodium Bicarbonate → 1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

HRID 1597207Notes

Reaction equation

HRID 1597207 reaction equation
Br.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:4][C:3]1=[O:11].C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:4][C:3]1=[O:11]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 216992747-Azaoxindole hydrobromide

Product 1

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 7-azaoxindole hydrobromide (800 mg, 3.7 mmol), (Tet.Let. 1987, 28, 4027), in methylene chloride (10 ml) was adjusted to pH9 with saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The organic layers were combined, washed with brine, dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 7-azaoxindole free base (238 mg, 48%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-a83268df16eb47df8d220dcba24c69c9
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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