Phosphorus oxychloride → HCID 13713228, compound

HRID 1194525Notes

Reaction equation

HRID 1194525 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. customThe excess phosphorous oxychloride is then removed
  2. customby evaporating under reduced pressure
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with ice-cold saturated sodium bicarbonate aqueous solution
  5. customThe chloroform layer is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-17357a396462486bb5b998a84256d1f6
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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