8-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine → 8-Hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053040Notes

Reaction equation

HRID 2053040 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:12]=[C:13]([CH2:15][O:16][CH3:17])[CH:14]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[C:10]2[N:11]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:12]=[C:13]([CH2:15][O:16][CH3:17])[CH:14]=1

Participants

4

Reactant 1

HCID 218739748-Benzyloxy-6-methoxymethyl-2,3-dimethylimidazo[1,2-a]pyridine

Product 1

HCID 692875158-Hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridineYield 57.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.0 g (10.1 mmol) 8-benzyloxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine in 50 ml ethanol is hydrogenated over 0.3 g 10% Pd/C (1 bar H2) for 1 h. The catalyst is filtered off and the filtrate is evaporated. The residue is crystallized from methanol/diethyl ether to give 1.2 g (57%) of the title compound as a colourless solid (m.p. 164-165° C.).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-027db844a6cc4d1cbf76dbab3d2daa33
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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