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

HRID 1906177Notes

Reaction equation

HRID 1906177 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

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-88c01dc36d094ea39332f5883ba1b9af
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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