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

HRID 883906Notes

Reaction equation

HRID 883906 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][N: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 178517692HCID 178517692, compound

Product 1

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

Conditions

Temperature
80 °C

Procedure

The product from Example 36d (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-37b0ea41be9c41638601733c59d369dd
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…