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

HRID 2197995Notes

Reaction equation

HRID 2197995 reaction equation
[N:1]1[C:10]2[N:9]=[CH:8][CH:7]=[C:6](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:10]1[N:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516463HCID 178516463, compound

Product 1

HCID 122042345-Chloro-1,6-naphthyridineYield 87%

Conditions

Temperature
80 °C

Procedure

The product from Example 228d (0.250 g, 1.71 mmol) was combined with phosphorous oxychloride (4 mL) and heated under a nitrogen atmosphere at 80° C. for 18.5 h followed by vacuum distillation to remove the volatiles. The residue was slurried with ice and made basic (pH 7-8) with concentrated ammonium hydroxide. The title compound was collected by vacuum filtration, water washed and dried under vacuum to give a gray solid (0.245 g, 87%) sufficiently pure for use as isolated.

Workup

  1. distillationfollowed by vacuum distillation
  2. customto remove the volatiles
  3. filtrationThe title compound was collected by vacuum filtration, water
  4. washwashed
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1b47100f0dac4181b10d015540317404
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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