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

HRID 340470Notes

Reaction equation

HRID 340470 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-286bdb85b6d34df5818e8369f9297370
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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