Acetic Acid → HCID 13336719, compound

HRID 1906183Notes

Reaction equation

HRID 1906183 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[C:3]=1[CH3:15].Br.[C:17](O)(=[O:19])[CH3:18]>>[C:17]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:4]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:15])(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 9815717HCID 9815717, compound2×

Product 1

HCID 13336719HCID 13336719, compoundYield 65%

Procedure

3-Hydroxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one, prepared as described under (N), (2 g) is dissolved in glacial acetic acid containing about 1% w/v of hydrogen bromide and the solution is refluxed for 2 hours. The resultant mixture is subjected to rotary evaporation and the residue crystallised from aqueous ethonal to give 1-(5'-acetoxypentyl)-3-hydroxy-2-methylpyrid-4one in 65% yield, m.p. 132°-133° C., δmax (nujol) 1520, 1540, 1580, 1635, 1735 cm-1 and δ(d6DMSO), 1.6 (m, 6H), 2.1 (s, 3H), 2.4 (s, 3H), 4.05 (m, 4H), 6.4 (d, 1H), 7.3 (d, 1H).

Workup

  1. temperaturethe solution is refluxed for 2 hours
  2. customThe resultant mixture is subjected to rotary evaporation
  3. customthe residue crystallised from aqueous ethonal

Sources & evidence

ORD record
ord-3e30d70f98fa4bcc898a4d77852dcaa3
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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