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

HRID 1249804Notes

Reaction equation

HRID 1249804 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[CH:18]([O:21][CH3:22])[CH2:19][CH3:20].[ClH:23]>CO.O.[Pd]>[ClH:23].[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:21][CH3:22])[CH2:19][CH3:20]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 186787911,6-Dimethyl-2-(1-methoxypropyl)-3-benzyloxy-pyridin-4(1H)-one

Product 1

HCID 186788091,6-Dimethyl-2-(1-methoxypropyl)-3-hydroxy-pyridin-4(1H)-one hydrochlorideYield 79.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1,6-Dimethyl-2-(1-methoxypropyl)-3-benzyloxy-pyridin-4-(1H)-one (1.65 g, 5.5 mmol) was dissolved in methanol (30 ml)/water (10 ml) and adjusted to pH 1 with concentrated hydrochloric acid prior to hydrogenolysis for 4 hours in the presence of 5% Pd/C catalyst (0.35 g). Filtration followed by rotary evaporation gave the crude product as a white solid. Recrystallization from methanol/diethyl ether gave the pure title compound (1.08 g, 79.3%) as a white crystalline solid. m.p. 225-227° C.

Workup

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

Sources & evidence

ORD record
ord-1132c3a5cf634e7097eb14ad8617d0ad
Source dataset
uspto-grants-2002_01
Patent number
US06335353B1

Reaction notes

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