Triethylamine → 1-Acetyl-3-(benzyloxy)-2-methylpyridin-4(1H)-one

HRID 355281Notes

Reaction equation

HRID 355281 reaction equation
[CH2:1]([O:8][CH:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]=[C:10]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Br)(=[O:19])[CH3:18].C(N(CC)CC)C>CC(C)=O>[C:17]([N:11]1[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]1[CH3:16])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10482Acetyl bromideHCID 693437942-Methyl-3-(phenylmethoxy)-4(3H)-pyridinone

Product 1

HCID 186887761-Acetyl-3-(benzyloxy)-2-methylpyridin-4(1H)-oneYield 64.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1 3-Benzyloxy-2-methylpyrid-4-one (4 g) is dissolved in dry acetone (100 ml). Acetylbromide (3 g) and triethylamine (2.7 g) are added and the resulting mixture is mechanically stirred overnight. The mixture is then filtered and the filtrate is rotary evaporated to dryness. The residue is dissolved in methylene chloride and washed with dilute hydrochloric acid (pH 3.0), then twice with water, and is dried over Na2SO4 and rotary evaporated to yield a solid residue. Recrystallisation of this residue from an ethylacetate/hexane mixture gives 1-acetyl-3-benzyloxy-2-methylpyrid-4-one as an oil (3.1 g).

Workup

  1. filtrationThe mixture is then filtered
  2. customthe filtrate is rotary evaporated to dryness
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with dilute hydrochloric acid (pH 3.0)
  5. dry with materialtwice with water, and is dried over Na2SO4
  6. customrotary evaporated
  7. customto yield a solid residue
  8. customRecrystallisation of this residue from an ethylacetate/hexane mixture

Sources & evidence

ORD record
ord-a037f7bcfe7c47cf8468dd12e62eb72f
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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