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

HRID 1906171Notes

Reaction equation

HRID 1906171 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-6e9525b9191d448a8bfaae6cd7b9a16a
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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