1,6-Dimethyl-2-methoxymethyl-3-benzyloxypyridin-4(1H)-one hydrochloride → 1,6-Dimethyl-2-methoxymethyl-3-hydroxy-pyridin-4(1H)-one hydrochloride

HRID 1634613Notes

Reaction equation

HRID 1634613 reaction equation
[ClH:1].[CH3:2][N:3]1[C:8]([CH3:9])=[CH:7][C:6](=[O:10])[C:5]([O:11]CC2C=CC=CC=2)=[C:4]1[CH2:19][O:20][CH3:21]>CO.O.[Pd]>[ClH:1].[CH3:2][N:3]1[C:8]([CH3:9])=[CH:7][C:6](=[O:10])[C:5]([OH:11])=[C:4]1[CH2:19][O:20][CH3:21]

Participants

5

Reactant 1

HCID 699544351,6-Dimethyl-2-methoxymethyl-3-benzyloxypyridin-4(1H)-one hydrochloride

Product 1

HCID 186788241,6-Dimethyl-2-methoxymethyl-3-hydroxy-pyridin-4(1H)-one hydrochlorideYield 86.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,6-Dimethyl-2-methoxymethyl-3-benzyloxy-pyridin-4(1H)-one hydrochloride (1.55 g, 5 mmol) was dissolved in methanol (40 ml)/water (10 ml) and hydrogenated for 4 hours in the presence of 5% Pd/C (0.3 g). Following filtration the filtrate was concentrated in vacuo and the crude material recrystallised from methanol/diethyl ether gave the pure title compound (0.95 g, 86.5%) as a white crystalline solid. m.p. 156-159° C.

Workup

  1. filtrationfiltration the filtrate
  2. concentrationwas concentrated in vacuo
  3. customthe crude material recrystallised from methanol/diethyl ether

Sources & evidence

ORD record
ord-1a7d965f111a401aacbf90a0671225b2
Source dataset
uspto-grants-2003_01
Patent number
US06506911B2

Reaction notes

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