Hydrochloric Acid → 1,6-Dimethyl-2-(1-ethoxyethyl)-3-hydroxy-pyridin-4(1h)-one hydrochloride

HRID 1279416Notes

Reaction equation

HRID 1279416 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[C:4]([O:10]CC2C=CC=CC=2)=[C:3]1[CH2:18][O:19][CH2:20][CH3:21].[ClH:22].[CH2:23](O)C>[Pd]>[ClH:22].[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[C:4]([OH:10])=[C:3]1[CH:18]([O:19][CH2:20][CH3:21])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 186788281,6-Dimethyl-2-(1-ethoxymethyl)-3-benzyloxy-pyridin-4(1H)-one

Product 1

HCID 186788011,6-Dimethyl-2-(1-ethoxyethyl)-3-hydroxy-pyridin-4(1h)-one hydrochlorideYield 83.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1,6-Dimethyl-2-(1-ethoxymethyl)-3-benzyloxy-pyridin-4(1H)-one (3.65 g, 12 mmol) was dissolved in 40 ml of ethanol and adjusted to pH 1 with concentrated hydrochloric acid prior to hydrogenolysis for 4 hours in the presence of 5% Pd/C catalyst (0.8 g). Filtration followed by rotary evaporation gave the crude product as a white solid. Recrystallization from ethanol/diethyl ether gave the pure title compound (2.48 g, 83.3%) as a white crystalline solid. m.p. 195-199° C.

Workup

  1. filtrationFiltration
  2. customfollowed by rotary evaporation
  3. customgave the crude product as a white solid
  4. customRecrystallization from ethanol/diethyl ether

Sources & evidence

ORD record
ord-7df84c65466c41a4836040bda470bb5a
Source dataset
uspto-grants-2002_09
Patent number
US06448273B1

Reaction notes

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