Hydrochloric Acid → HCID 23078428, compound

HRID 229033Notes

Reaction equation

HRID 229033 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]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[OH-:20].[Na+].Cl>ClCCl>[C:14]1([C:12]2[C:11]([OH:20])=[CH:8][C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[N:1]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 107572-ChloroacetophenoneHCID 14798Sodium HydroxideHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 23078428HCID 23078428, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-pyridine-3-carbaldehyde (100 mg) and 2-chloro-1-phenyl-ethanone (127 mg) were suspended in a 5 N aqueous sodium hydroxide solution (0.6 ml), and the suspension was hermetically sealed and, in this state, was allowed to stand for 3 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-phenyl-[1,8]naphthyridin-3-ol (23 mg, yield 13%).

Workup

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

Sources & evidence

ORD record
ord-86778dcdb2d24ed99375f8c4bd7c3611
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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