Phosphorus oxychloride → 5-Chloro-1,6-naphthyridine

HRID 1615693Notes

Reaction equation

HRID 1615693 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 55203681,6-naphthyridin-5(6H)-one

Product 1

HCID 122042345-Chloro-1,6-naphthyridine

Conditions

Temperature
0 °C

Procedure

A solution of 1,6-naphthyridin-5(6H)-one (3.2 g, 21.9 mmol) in phosphoryl trichloride (50 mL) was stirred at 100° C. overnight. The volatiles were removed under reduced pressure. The residue was cooled to 0° C. NaOH (saturated aqueous solution) was added to adjust the pH to 9. The mixture was extracted with EtOAc (200 mL×3). The combined organic layers were dried over sodium sulfate and concentrated to give 3.3 g of the crude product as a yellow solid. ESI MS: m/z 165 [M+H]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionNaOH (saturated aqueous solution) was added
  3. extractionThe mixture was extracted with EtOAc (200 mL×3)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71fc5828a71646b0bed8cdaf3e9a4746
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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