Hydrochloric Acid → 2-Pyridin-2-yl-[1,8]naphthyridin-3-ol

HRID 229031

Reaction equation

HRID 229031 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Br.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)=O.[OH-:21].[Na+].Cl>ClCCl>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[C:12]([OH:21])=[CH:8][C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

Product 1

HCID 1358548402-Pyridin-2-yl-[1,8]naphthyridin-3-olYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-pyridine-3-carbaldehyde (200 mg) and 2-(bromoacetyl)pyridine hydrobromide (506 mg) were suspended in a 5 N aqueous sodium hydroxide solution (1 ml), and the suspension was hermetically sealed and, in this state, was allowed to stand for 2 days. The reaction solution was neutralized with 10% hydrochloric acid, dichloromethane was then added thereto, and the mixture was extracted. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give 2-pyridin-2-yl-[1,8]naphthyridin-3-ol (48 mg, yield 13%).

Workup

  1. customthe suspension was hermetically sealed and, in this state
  2. additionwas then added
  3. extractionthe mixture was extracted
  4. washThe dichloromethane layer was washed with water and saturated brine
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e888ea269f514af298f9e08656f3d610
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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