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

HRID 2358830Notes

Reaction equation

HRID 2358830 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-68da5c5aef554ee4a73ac0927499c834
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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