Phosphorus oxychloride → HCID 86615212, compound

HRID 733753Notes

Reaction equation

HRID 733753 reaction equation
[CH3:1][N:2]1[C:10]2[C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][NH:7][C:6](=O)[C:5]=2[CH:4]=[C:3]1[CH3:16].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:6]1[C:5]2[CH:4]=[C:3]([CH3:16])[N:2]([CH3:1])[C:10]=2[C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68866324HCID 68866324, compound

Product 1

HCID 86615212HCID 86615212, compound

Procedure

A solution of methyl 1,2-dimethyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (1.311 g) in phosphorus oxychloride (7 ml) was heated under reflux for four hours, then evaporated under reduced pressure. The residual liquid was added to a mixture of ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with a further portion of ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate and then water. After filtering the water and ethyl acetate mixture, the organic phase washed with brine, dried (MgSO4) and evaporated. Purification by chromatography on silica gel (ethyl acetate/toluene) afforded the title compound as a pale cream solid 1.027 g.

Workup

  1. temperatureunder reflux for four hours
  2. customevaporated under reduced pressure
  3. additionThe residual liquid was added to a mixture of ethyl acetate and saturated aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with a further portion of ethyl acetate
  5. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate
  6. filtrationAfter filtering the water and ethyl acetate mixture
  7. washthe organic phase washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customPurification by chromatography on silica gel (ethyl acetate/toluene)

Sources & evidence

ORD record
ord-574cd88d8a8c4cd5ac3cae6f69e53513
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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