8-Methylimidazo(1,2-a)pyridine → 8-Methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
Reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(O)CCC.[Ni]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]2[CH:8]=[CH:9][N:10]=[C:3]12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
1 g of 8-methylimidazo[1,2-a]pyridine [3-1] was dissolved in 20 mL of 1-butanol, and a catalytic amount of Raney nickel of was added thereto. The mixture was stirred under a hydrogen atmosphere (5 atmospheric pressure) at 65° C. for 4 days. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, and washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 823.3 mg of 8-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [46-1].