Hydrochloric Acid → 2-Methyl-1,8-naphthyridin-3-ol

HRID 228900Notes

Reaction equation

HRID 228900 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:11][C:12](=O)[CH3:13].Cl.[OH-:16].[Na+]>>[CH3:13][C:12]1[C:11]([OH:16])=[CH:8][C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 230782942-Methyl-1,8-naphthyridin-3-olYield 40%

Procedure

2-Amino-pyridine-3-carbaldehyde (2.0 g) and chloroacetone (1.5 g) were suspended in a 5 N aqueous sodium hydroxide solution (10 ml) and was allowed to stand in a hermetically sealed state for 3 days. The reaction solution was neutralized with 10% hydrochloric acid, and the precipitated crystal was then collected by filtration. Isopropanol was added to the crystal, and the mixture was heated under reflux. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation. Hexane was added to the residue, and the precipitated crystal was collected by filtration and was washed with hexane to give 2-methyl-[1,8]naphthyridin-3-ol (1.05 g, yield 40%).

Workup

  1. filtrationthe precipitated crystal was then collected by filtration
  2. additionIsopropanol was added to the crystal
  3. temperaturethe mixture was heated
  4. temperatureunder reflux
  5. customthe solvent was then removed by distillation
  6. additionHexane was added to the residue
  7. filtrationthe precipitated crystal was collected by filtration
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-b029443dce724409aa24acac54e5274d
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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