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

HRID 374443Notes

Reaction equation

HRID 374443 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-].[Na+].[CH2:19]([CH2:21][NH2:22])[OH:20].Cl>C(O)C.C(OCC)C.O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:22]([CH2:21][CH2:19][OH:20])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

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-oneYield 44.94%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the product from (1) in ethanol:water (300 ml:300 ml) containing 5% aqueous sodium hydroxide (2 ml) was treated with ethanolamine (17 ml) and then refluxed for 18 hours with rapid stirring. The resultant solution was cooled and adjusted to pH 1 with concentrated hydrochloric acid. The solid which formed on cooling was extracted with hot absolute ethanol and the precipitate obtained on cooling was taken up in diethylether, the solution being filtered and evaporated to dryness by rotary evaporation to give the title compound in 44.94% yield, m.p. 191.5°-193° C.

Workup

  1. temperaturerefluxed for 18 hours with rapid stirring
  2. customThe solid which formed
  3. temperatureon cooling
  4. extractionwas extracted with hot absolute ethanol
  5. customthe precipitate obtained
  6. temperatureon cooling
  7. filtrationthe solution being filtered
  8. customevaporated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-cd034d164adc477c831d76eaf5b14afe
Source dataset
uspto-grants-1996_01
Patent number
US05480894

Reaction notes

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