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

HRID 1381166Notes

Reaction equation

HRID 1381166 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-4e6693f8ca7c4aecb087718f4781e1c6
Source dataset
uspto-grants-1986_04
Patent number
US04585780

Reaction notes

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