3-Benzyloxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one → 3-Hydroxy-1-(2-hydroxyethyl)-2-methyl-4(1H)-pyridinone

HRID 355283Notes

Reaction equation

HRID 355283 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH3:19])C1C=CC=CC=1>Br>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][OH:18])[C:10]=1[CH3:19]

Participants

3

Reactant 1

HCID 4046803-Benzyloxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one

Product 1

HCID 944143-Hydroxy-1-(2-hydroxyethyl)-2-methyl-4(1H)-pyridinoneYield 61.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3-Benzyloxy-1-(2'-hydroxyethyl)-2-methylpyrid-4-one (2 g) is added to concentrated hydrobromic acid (10 ml) and the mixture is heated on a steam bath for 30 minutes. The resultant product is then recrystallised from water to yield 3-hydroxy-1(2'-hydroxyethyl)-2-methylpyrid-4-one as white crystals (0.8 g), m.p. 164°-165° C.; νmax (nujol) 1630, 3150, 3350 cm-1 ; δ(dbDMSO), 2.5 (s, 3H), 3.7 (t, 2H), 4.35 (t, 2H), 7.25 (3, 1H), 8.15 (d, 1H).

Workup

  1. temperaturethe mixture is heated on a steam bath for 30 minutes
  2. customThe resultant product is then recrystallised from water

Sources & evidence

ORD record
ord-6463b3415ad348b4a54015fc693148c8
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

Loading…