Phosphorus oxychloride → 1-Chloro-2,7-naphthyridine

HRID 1723017Notes

Reaction equation

HRID 1723017 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517682HCID 178517682, compound

Product 1

HCID 130821701-Chloro-2,7-naphthyridineYield 68%

Conditions

Temperature
130 °C

Procedure

A pressure bottle, equipped with a magnetic stirrer, was charged with 1-hydroxy-2,7-naphthyridine (2.6 g, 17.8 mmol) and 100 mL of phosphorous oxychloride. The bottle was sealed and heated at 130° C. overnight. Upon cooling, the bottle was opened and the excess POCl3 was removed by evaporation in vacuo. The residue was treated with excess saturated Na2CO3 and extracted twice with CHCl3. The organic layer was washed with brine and dried (Na2SO4). Evaporation of the solvent afforded the product as a light brown solid (2.0 g, 68%, purity 90-95% based on NMR). The product was of suitable purity for use in the next step.

Workup

  1. customA pressure bottle, equipped with a magnetic stirrer
  2. customThe bottle was sealed
  3. temperatureUpon cooling
  4. customthe excess POCl3 was removed by evaporation in vacuo
  5. additionThe residue was treated with excess saturated Na2CO3
  6. extractionextracted twice with CHCl3
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5ffb66c59a6d4d5482ea0ed95b2d6815
Source dataset
uspto-grants-1989_08
Patent number
US04859671

Reaction notes

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