Acetyl bromide → 1-Acetyl-3-hydroxypyrid-2-one
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureto cool
- extractionThe resulting suspension is extracted with methylene chloride
- dry with materialthe methylene chloride solution is dried over Na2SO4
- customevaporated
- customThe resultant residue is recrystallised from petroleum ether (80°-100° C.)
Sources & evidence
- ORD record
- ord-e4ca0c3e08964a5b9c819985fe09a4a7
- Source dataset
- uspto-grants-2000_08
- Patent number
- USRE036831
Reaction notes
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