Ethanol → 1,2-Dihydro-5-methyl-2-oxo-1,6-naphthyridin-3-amidoxime

HRID 565381Notes

Reaction equation

HRID 565381 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].C(O)C.[CH3:13][C:14]1[N:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[C:17]([C:25]#[N:26])[C:18](=[O:24])[NH:19]2>O>[CH3:13][C:14]1[N:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[C:17]([C:25](=[N:2][OH:3])[NH2:26])[C:18](=[O:24])[NH:19]2

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57130685-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile

Product 1

HCID 1360252791,2-Dihydro-5-methyl-2-oxo-1,6-naphthyridin-3-amidoximeYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of hydroxylamine hydrochloride (4.17 g) in water (50 ml) was added sodium carbonate (3.18 g) with stirring under ice cooling. To the solution were subsequently added ethanol (200 ml) and 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile (3.70 g), and the mixture was refluxed for 2 hours. After distilling off the solvent under reduced pressure, water was added to the residue, and the precipitated crystals were separated by filtration. The product was washed with water, isopropanol, diisopropyl ether in this order, and dried to give 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridin-3-amidoxime (4.2 g). This compound was used in the next reaction without being purified.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationAfter distilling off the solvent under reduced pressure, water
  3. additionwas added to the residue
  4. customthe precipitated crystals were separated by filtration
  5. washThe product was washed with water, isopropanol, diisopropyl ether in this order
  6. customdried

Sources & evidence

ORD record
ord-579ef4d89f894f109ee1d96fbce47132
Source dataset
uspto-grants-2001_01
Patent number
US06172079B2

Reaction notes

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