Phosphorus oxychloride → 2-Chloro-1,6-naphthyridine

HRID 1173122Notes

Reaction equation

HRID 1173122 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5896741,6-Naphthyridin-2(1H)-One

Product 1

HCID 135319672-Chloro-1,6-naphthyridineYield 58.45%

Conditions

Temperature
120 °C

Procedure

1,6-Naphthyridine-2-one (1.0 g, J. Org. Chem. 4744 (1990)) was dissolved in phosphorous oxychloride (19 ml), followed by heating under reflux at 120° C. for 2 hours. After cooling, the solvent was evaporated, and the residue was basified with water and potassium carbonate. Then, the mixture was extracted with ethyl acetate, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (0.658 g, 58.45%) as orange crystals.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. extractionThen, the mixture was extracted with ethyl acetate
  5. washthe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2f864acd90334f0488ce84625148b9c4
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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