Sodium Bicarbonate → 5-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-one

HRID 2394335Notes

Reaction equation

HRID 2394335 reaction equation
N[C:2]1[C:3]([CH2:9][C:10]#[N:11])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C([O-])(O)=[O:13].[Na+]>Cl>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][N:6]=1)[NH:11][C:10](=[O:13])[CH2:9]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18973056HCID 18973056, compound

Product 1

HCID 189730325-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-oneYield 46%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(5-Amino-2-chloro-4-pyridyl)acetonitrile (1.40 g, 8.4 mmol) was taken up in 6N HCl solution (100 mL) and heated between 50° and 100° C. for 2 hours. After cooling, the solution was adjusted to pH 7 by addition of solid NaHCO3 and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was subjected to flash chromatography on silica gel using ethyl acetate as eluant. (Some methanol was used to help dissolve the solid). Fractions containing the desired product were combined and concentrated to leave the title compound as a solid (650 mg, 46%), m.p. 230° C. (dec.) The NMR spectrum indicated that this material contained a small amount of the by-product, 2-amino-5-chloro-6-azaindole in addition to the title compound. Nonetheless, this material was used in the next step without further purification.

Workup

  1. temperatureheated between 50° and 100° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionto help dissolve the solid)
  8. additionFractions containing the desired product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-23844943d8244458a3483e8e1cb172c2
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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