Hydrochloric Acid → 8-Hydroxy-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine hydrochloride

HRID 544463Notes

Reaction equation

HRID 544463 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[ClH:19]>[Pd].C(O)C>[ClH:19].[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:10]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 139003368-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 139003388-Hydroxy-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-benzyloxy-2-methyl-imidazo[1,2-a]pyridine (5.9 g), 6.1 N HCl(4.2 ml), 10% Palladium-on-charcoal (5.9 g) and 240 ml ethanol was hydrogenated under a H2 -pressure of about 3.5 kg/cm2 for 22 hrs. at room temperature, after which period a further 2 g of fresh catalyst was added and hydrogenation continued for another 45 hrs. After filtration and evaporation of the solvent at the reduced pressure, the title compound is obtained as a pale yellow solid with m.p. 140°-152° C.

Workup

  1. customfor 22 hrs
  2. filtrationAfter filtration and evaporation of the solvent at the reduced pressure

Sources & evidence

ORD record
ord-f96b8ed5be5a44188256a423add30177
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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