Hydrochloric Acid → 3-Benzyloxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one

HRID 355282Notes

Reaction equation

HRID 355282 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:17][CH2:18][CH2:19][NH2:20].[OH-].[Na+].Cl>O.C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:20]([CH2:19][CH2:18][OH:17])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Benzyloxy-2-methyl-4-pyrone (4.8 g), prepared as described under Example 10, and 2-hydroxyethylamine (1.22 g) are dissolved in water (220 ml) and ethanol (100 ml) containing sodium hydroxide (2 g) is added. The mixture is stirred at room temperature for 6 days and is then acidified with concentrated hydrochloric acid to pH 2, and evaporated to dryness. The resulting colourless solid is washed with water and extracted into chloroform (2×50 ml). The chloroform extracts are combined, dried over magnesium sulphate, and evaporated to yield 3-benzyloxy-1-(2'-hydroxyethyl)-2-methylpyrid-4-one, as a white solid (3.4 g), m.p. 198°-199° C.

Workup

  1. additionis added
  2. customevaporated to dryness
  3. washThe resulting colourless solid is washed with water
  4. extractionextracted into chloroform (2×50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-3e934bc9531146fa88c6b16b8cb90386
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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