Phosphorus oxychloride → HCID 13713228, compound

HRID 1905673Notes

Reaction equation

HRID 1905673 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][CH2:14][CH2:15][C:3]=12.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469462HCID 178469462, compound

Product 1

HCID 13713228HCID 13713228, compound

Procedure

A mixture of 2.6 g of ethyl 6,7-dihydro-4-hydroxy-5H-cyclopenta[b]pyridine-3-carboxylate [J. Heterocyclic Chem. 12, 1245 (1975)] and 100 mL of phosphorous oxychloride is refluxed for 2.5 hours. The excess phosphorous oxychloride is then removed by evaporating under reduced pressure. The residue is dissolved in chloroform and washed with ice-cold saturated sodium bicarbonate aqueous solution. The chloroform layer is separated, dried over magnesium sulfate, passed through a short silica gel column and evaporated to dryness to yield ethyl 4-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylate.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. customThe excess phosphorous oxychloride is then removed
  3. customby evaporating under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with ice-cold saturated sodium bicarbonate aqueous solution
  6. customThe chloroform layer is separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-7a760b93d0d34dd7b6b16f08436c781d
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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