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

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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 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

distillationfollowed by vacuum distillation
customto remove the volatiles
filtrationThe title compound was collected by vacuum filtration, water
washwashed
customdried under vacuum

Sources & evidence

ORD record: ord-37b0ea41be9c41638601733c59d369dd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236950B2

Reaction notes

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