1,6-dimethyl-2-(1-methoxyethyl)-3-benzyloxy-pyridin-4(1H)-one hydrochloride → 1,6-Dimethyl-2-(1-methoxyethyl)-3-hydroxy-pyridin-4(1H)-one hydrochloride

HRID 1249802Notes

Reaction equation

HRID 1249802 reaction equation
[ClH:1].CN1C(C)=CC(=O)C(O)=C1COC.Cl.[CH3:16][N:17]1[C:22]([CH3:23])=[CH:21][C:20](=[O:24])[C:19]([O:25]CC2C=CC=CC=2)=[C:18]1[CH:33]([O:35][CH3:36])[CH3:34]>[Pd]>[ClH:1].[CH3:16][N:17]1[C:22]([CH3:23])=[CH:21][C:20](=[O:24])[C:19]([OH:25])=[C:18]1[CH:33]([O:35][CH3:36])[CH3:34]

Participants

4

Reactant 2

HCID 186787961,6-dimethyl-2-(1-methoxyethyl)-3-benzyloxy-pyridin-4(1H)-one hydrochlorideHCID 186788241,6-Dimethyl-2-methoxymethyl-3-hydroxy-pyridin-4(1H)-one hydrochloride

Product 1

HCID 186787901,6-Dimethyl-2-(1-methoxyethyl)-3-hydroxy-pyridin-4(1H)-one hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In an analogous hydrogenation procedure in the preparation of 1,6-dimethyl-2-methoxymethyl-3-hydroxy-pyridin-4(1H)-one hydrochloride using 1,6-dimethyl-2-(1-methoxyethyl)-3-benzyloxy-pyridin-4(1H)-one hydrochloride (1.62 g, 5 mmol) and 5% Pd/C catalyst (0.35 g) yield the title compound 1.06 g (90%) after recrystallisation from methanol/diethyl ether, as a white crystalline solid. m.p. 205-207° C.

Sources & evidence

ORD record
ord-a7a634b781ef4f0abda09dd948d91247
Source dataset
uspto-grants-2002_01
Patent number
US06335353B1

Reaction notes

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