Phosphorus oxychloride → Ethyl 4-chloro-1,6-naphthyridine-3-carboxylate

HRID 1633246Notes

Reaction equation

HRID 1633246 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469618HCID 178469618, compound

Product 1

HCID 17608818Ethyl 4-chloro-1,6-naphthyridine-3-carboxylate

Procedure

A mixture of 9.3 g of ethyl 4-hydroxy-1,6-naphthyridine-3-carboxylate (prepared according to J. Org. Chem. 15, 1224 (1950)) and 56 ml of phosphorous oxychloride is refluxed for 2 hours 40 minutes, then evaporated to dryness and the residue is treated with cold dilute ammonium hydroxide and methylene chloride. Insoluble material is removed by filtration, then organic layer is separated, washed with brine, dried over sodium sulfate and evaporated to dryness to yield ethyl 4-chloro-1,6-naphthyridine-3-carboxylate.

Workup

  1. temperatureis refluxed for 2 hours 40 minutes
  2. customevaporated to dryness
  3. additionthe residue is treated with cold dilute ammonium hydroxide and methylene chloride
  4. customInsoluble material is removed by filtration
  5. customorganic layer is separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-2979eeebf52249f0b3de441b46cc3053
Source dataset
uspto-grants-1984_10
Patent number
US04479955

Reaction notes

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