Water → 7-Fluoro-1,5-naphthyridin-2(1H)-one

HRID 1510736Notes

Reaction equation

HRID 1510736 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-])=[N:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=[O:20])=CC=1.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[NH:9]2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 578152157-Fluoro-1,5-naphthyridine 1-oxide

Product 1

HCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-oneYield 23.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 60 mg of 7-fluoro-1,5-naphthyridine 1-oxide in 1.6 mL of chloroform, 84 mg of p-toluenesulfonyl chloride, 171 mg of potassium carbonate and 0.5 mL of water were added, and the mixture was stirred at room temperature overnight. The solid was filtered off, and purified by silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of chloroform:methanol=10:1 to obtain 14 mg of 7-fluoro-1,5-naphthyridin-2(1H)-one as a white solid.

Workup

  1. filtrationThe solid was filtered off
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fe736c2330f44b88afa69d899ef154c
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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