Sodium methanolate methanol → 7-Methoxy-1,5-naphthyridin-2(1H)-one

HRID 385487Notes

Reaction equation

HRID 385487 reaction equation
[NH2:1][C:2]1[C:3](/[CH:10]=[CH:11]/[C:12]([O:14]CC)=O)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C[O-].[Na+].CO>CO>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:10]=[CH:11][C:12](=[O:14])[NH:1]2)=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanol3×HCID 68105232ethyl (2E)-3-(3-amino-5-methoxypyridin-2-yl)acrylate

Product 1

HCID 578154107-Methoxy-1,5-naphthyridin-2(1H)-oneYield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.51 g of ethyl (2E)-3-(3-amino-5-methoxypyridin-2-yl)acrylate in 6 mL of methanol, 0.53 g of a 28% sodium methoxide/methanol solution was added at room temperature, and the mixture was heated under reflux while stirring for 2 hours 20 minutes. Thereto was added 0.53 g of a 28% sodium methoxide/methanol solution, and the mixture was heated under reflux while stirring for 1 hour 45 minutes. Thereto was further added 0.53 g of a 28% sodium methoxide/methanol solution, and the mixture was heated under reflux while stirring for 1 hour 15 minutes. The reaction mixture was cooled to room temperature, the solvent was then distilled off under reduced pressure, and the resultant residue was charged with ethyl acetate and water and adjusted to pH 7.2 with 1 mol/L hydrochloric acid. The solvent was distilled off under reduced pressure, and the solid was filtered off and washed with water and diethyl ether to obtain 0.25 g of 7-methoxy-1,5-naphthyridin-2(1H)-one as a light brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux
  5. stirringwhile stirring for 1 hour 45 minutes
  6. temperaturethe mixture was heated
  7. temperatureunder reflux
  8. stirringwhile stirring for 1 hour 15 minutes
  9. distillationthe solvent was then distilled off under reduced pressure
  10. additionthe resultant residue was charged with ethyl acetate and water
  11. distillationThe solvent was distilled off under reduced pressure
  12. filtrationthe solid was filtered off
  13. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-61001d565cee4edcaf8efa68b30f3cb8
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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