Water → 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one

HRID 385509Notes

Reaction equation

HRID 385509 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:18])[N:9]2[CH2:12][CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:4][CH:3]=1.[CH3:19][O-:20].[Na+].CO.O>CO>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([O:20][CH3:19])[N:11]=2)[CH:6]=[CH:7][C:8]1=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 23694274Sodium methanolate methanolHCID 578152377-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 578153441-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.5 g of 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one in 30 mL of methanol, 5.4 g of a 28% sodium methoxide/methanol solution was added, and the mixture was heated under reflux while stirring for 3 hours 40 minutes. The reaction mixture was cooled to room temperature, then water was added thereto, and the solvent was then distilled off under reduced pressure. To the resultant residue, water, a saturated aqueous ammonium chloride solution and chloroform were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.9 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one as a yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. distillationthe solvent was then distilled off under reduced pressure
  4. additionTo the resultant residue, water, a saturated aqueous ammonium chloride solution and chloroform were added
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-88adfe7ccad844c4898c753a3b4bad5e
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

Loading…