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

HRID 1906178Notes

Reaction equation

HRID 1906178 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.C(OC1C(=O)C=COC=1C)C1C=CC=CC=1.C([N:36]1C=CC(=O)[C:38]([OH:43])=[C:37]1C)(=O)C.OCCN.[OH-].[Na+].Cl>O.C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:36]([CH2:37][CH2:38][OH:43])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 14798Sodium HydroxideHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 867413491-acetyl-3-hydroxy-2-methylpyrid-4-one 3-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 (J), 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-9fd7b5a2916b4eb38521e5e1ce96e66e
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

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