p-Toluenesulfonic acid monohydrate → 1,6-naphthyridin-5(6H)-one

HRID 1772015Notes

Reaction equation

HRID 1772015 reaction equation
CO[CH:3](OC)[CH2:4][C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N:13]1[C:5]2[CH:4]=[CH:3][NH:9][C:7](=[O:8])[C:6]=2[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 134111212-(2,2-Dimethoxyethyl)nicotinamide

Product 1

HCID 55203681,6-naphthyridin-5(6H)-oneYield 66.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(2,2-dimethoxyethyl)nicotinamide (8.33 g, 39.7 mmol) and TsOH.H2O (940 mg) in toluene (100 mL) was refluxed for 14 h. Toluene was removed under reduced pressure, then the residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 1:1 and with EtOAc) to yield 1,6-naphthyridin-5(6H)-one as a light yellow solid (3.87 g, yield 66%). ESI MS: m/z 147 [M+H]+.

Workup

  1. temperaturewas refluxed for 14 h
  2. customToluene was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with PE/EtOAc v/v 1:1 and with EtOAc)

Sources & evidence

ORD record
ord-295b671ad89440a28a3ca37331c75bc9
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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