Hydrochloric Acid → 2-Ethyl-[1,6]naphthyridin-3-ol

HRID 229040Notes

Reaction equation

HRID 229040 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.Br[CH2:11][C:12](=O)[CH2:13][CH3:14].[OH-:16].[Na+].Cl>>[CH2:13]([C:12]1[C:11]([OH:16])=[CH:8][C:3]2[C:2](=[CH:7][CH:6]=[N:5][CH:4]=2)[N:1]=1)[CH3:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 131561-Bromo-2-butanoneHCID 14798Sodium HydroxideHCID 27610334-Aminonicotinaldehyde

Product 1

HCID 230783992-Ethyl-[1,6]naphthyridin-3-olYield 48%

Procedure

4-Amino-pyridine-3-carbaldehyde (100 mg) and 1-bromo-butan-2-one (124 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, the precipitate was then filtered, and the residue was washed with water and chloroform. The powder as the residue was dried under the reduced pressure to give 2-ethyl-[1,6]naphthyridin-3-ol (69 mg, yield 48%).

Workup

  1. customthe suspension was hermetically sealed and, in this state
  2. filtrationthe precipitate was then filtered
  3. washthe residue was washed with water and chloroform
  4. customThe powder as the residue was dried under the reduced pressure

Sources & evidence

ORD record
ord-4ed72ed1fcc042938e415882c50f640a
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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