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

HRID 1906179Notes

Reaction equation

HRID 1906179 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.; δmax (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-a93e42eaedea45c38b5582208422ee37
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

Loading…