Acetyl bromide → 1-Acetyl-3-hydroxypyrid-2-one

HRID 355276Notes

Reaction equation

HRID 355276 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](Br)(=[O:11])[CH3:10]>O>[C:9]([N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[C:2]1=[O:1])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 178516237HCID 178516237, compound

Product 1

HCID 133367261-Acetyl-3-hydroxypyrid-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-Dihydroxypyridine (5.55 g) is refluxed with acetylbromide (10 ml) overnight. The reaction mixture is allowed to cool and water (10 ml) is added. The resulting suspension is extracted with methylene chloride and the methylene chloride solution is dried over Na2SO4 and evaporated. The resultant residue is recrystallised from petroleum ether (80°-100° C.) to give 1-acetyl-3-hydroxypyrid-2-one as white crystals (2.8 g), m.p. 140°-141° C.; νmax (nujol) 1680, 3120 cm-1 ; δ(d6DMSO), 2.2 (s, 3H), 6.1 (t, 1H), 6.65 (m, 1H), 7.2 (d, 1H)

Workup

  1. temperatureto cool
  2. extractionThe resulting suspension is extracted with methylene chloride
  3. dry with materialthe methylene chloride solution is dried over Na2SO4
  4. customevaporated
  5. customThe resultant residue is recrystallised from petroleum ether (80°-100° C.)

Sources & evidence

ORD record
ord-09537393e73a48e4b68a6d983d0de14b
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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