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Hydrochloric Acid → 3-(Benzyloxy)-1,2-dimethylpyridin-4(1H)-one

HRID 465013
Notes
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Reaction equation

HRID 465013 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:18][NH2:19].[OH-].[Na+].Cl>O.C(O)C>[CH3:18][N:19]1[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]1[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 6364545Methylamine hydrochloride

Product 1

HCID 149562813-(Benzyloxy)-1,2-dimethylpyridin-4(1H)-oneYield 62.9%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

3-Benzyloxy-2-methyl-4-pyrone (4.8 g) and methylamine hydrochloride (1.56 g) are dissolved in water (200 ml) and ethanol (100 ml) containing sodium hydroxide (2 g) is added. The mixture is stirred at room temperature for 6 days and is then acidified with concentrated hydrochloric acid to pH 2, and evaporated to dryness. The resulting colourless solid is washed with water and extracted into chloroform (2×50 ml). The chloroform extracts are combined, dried over magnesium sulphate, and evaporated to yield 1,2-dimethyl-3-benzyloxypyrid-4-one (3.2 g).

Workup

  1. additionis added
  2. customevaporated to dryness
  3. washThe resulting colourless solid is washed with water
  4. extractionextracted into chloroform (2×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-89f4bfae287c4572bd13d91400b9fae5
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04550101

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes