Methanol → 1-methyl-6-nitro-1,8-naphthyridin-2(1H)-one

HRID 2406725Notes

Reaction equation

HRID 2406725 reaction equation
C[O-].[Na+].CO.[CH3:6][NH:7][C:8]1[C:13]([CH:14]=[CH:15][C:16](OCCCC)=[O:17])=[CH:12][C:11]([N+:23]([O-:25])=[O:24])=[CH:10][N:9]=1>O>[CH3:6][N:7]1[C:8]2[C:13](=[CH:12][C:11]([N+:23]([O-:25])=[O:24])=[CH:10][N:9]=2)[CH:14]=[CH:15][C:16]1=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 77522859n-Butyl 3-(2-(methylamino)-5-nitropyridin-3-yl)acrylate

Product 1

HCID 866838621-methyl-6-nitro-1,8-naphthyridin-2(1H)-oneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5M sodium methoxide (methanol solution) (0.5 ml) was added to a methanol solution (2 ml) containing n-butyl 3-(2-(methylamino)-5-nitropyridin-3-yl)acrylate (43 mg) obtained in the 1st step, followed by reflux for 3.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a white solid of 1-methyl-6-nitro-1,8-naphthyridin-2(1H)-one (24 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureby reflux for 3.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-5e4b6e384bbe461eb7898cc48ed8ad89
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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