Phosphorus oxychloride → HCID 21270439, compound

HRID 649589Notes

Reaction equation

HRID 649589 reaction equation
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][N:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C:3]=12.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][N:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469476HCID 178469476, compound

Product 1

HCID 21270439HCID 21270439, compound

Procedure

A mixture of 8.44 g of ethyl 4-hydroxy-5,7-dihydro-6-methoxycarbonylpyrrolo[3,4-b]pyridine-3-carboxylate and 50 ml of phosphorous oxychloride is refluxed for four hours, cooled to room temperature, and evaporated to dryness. The residue is taken up in methylene chloride, cooled by the addition of ice and basified with 10N sodium hydroxide. The layers are separated, and the aqueous phase is re-extracted with methylene chloride. The combined organic extract is dried, filtered, and evaporated to dryness to give ethyl 4-chloro-5,7-dihydro-6-methoxycarbonylpyrrolo[3,4-b]pyridine-3-carboxylate

Workup

  1. temperatureis refluxed for four hours
  2. customevaporated to dryness
  3. temperaturecooled by the addition of ice and basified with 10N sodium hydroxide
  4. customThe layers are separated
  5. extractionthe aqueous phase is re-extracted with methylene chloride
  6. extractionThe combined organic extract
  7. customis dried
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-a2238aa1468540b8b12ff7b37ee7dc81
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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