Phosphorus oxychloride → 4-Chloro-1,5-naphthyridine

HRID 513749

Reaction equation

HRID 513749 reaction equation
O=P(Cl)(Cl)[Cl:3].[N+:6]1([O-])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>>[Cl:3][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][N:11]=2)[N:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3392321-Oxo-1lambda~5~-1,5-naphthyridine

Product 1

HCID 5962624-Chloro-1,5-naphthyridineYield 36%

Conditions

Temperature
100 °C

Procedure

POCl3 (8.5 ml) was added to [1,5]naphthyridine 1-oxide 483 (0.85 g, 5.81 mmol) at 0° C. and the mixture was heated at 100° C. for 6 h. After cooling, the mixture was concentrated in vacuo, neutralized with NaHCO3 solution and the aqueous phase was extracted with EtOAc (40 ml). The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent to give the title compound (0.35 g, 36%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionthe aqueous phase was extracted with EtOAc (40 ml)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent

Sources & evidence

ORD record
ord-730196c261684ff9ad5320d336ba5b35
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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