Hydrochloric Acid → 2-Methyl-1,6-naphthyridin-3-ol

HRID 228904Notes

Reaction equation

HRID 228904 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.Cl[CH2:11][C:12](=O)[CH3:13].[OH-:15].[Na+].Cl>>[CH3:13][C:12]1[C:11]([OH:15])=[CH:8][C:3]2[C:2](=[CH:7][CH:6]=[N:5][CH:4]=2)[N:1]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 27610334-Aminonicotinaldehyde

Product 1

HCID 230784592-Methyl-1,6-naphthyridin-3-olYield 46%

Procedure

4-Amino-pyridine-3-carbaldehyde (1.0 g) and chloroacetone (0.7 g) were suspended in a 5 N aqueous sodium hydroxide solution (5 ml), and the suspension was allowed to stand in a sealed tube 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 collected 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-[1,6]naphthyridin-3-ol (0.60 g, yield 46%).

Workup

  1. filtrationthe precipitated crystal was then collected by filtration
  2. additionIsopropanol was added to the collected 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-2992e3e9308e4b308cd66b6d85c612ff
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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