HCID 17960600, compound → 2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methylaniline

Participants

Reaction Steps

To a solution of the title compound of Step A (0.5 g, 2.44 mmol) in ethanol (50 mL) was added palladium hydroxide (50 mg, 20 wt % on carbon). The flask was twice evacuated and flushed with nitrogen and then twice evacuated and flushed with hydrogen. The mixture was vigorously stirred under a balloon of hydrogen for 3 hours before being evacuated, exposed to air and filtered through a pad of Celite®. The solution was concentrated and filtered through a pad of silica gel, eluting with 5% then 10% methanol in dichloromethane, then 5% triethylamine, 10% methanol, 85% dichloromethane. The material eluting in triethylamine/methanol/dichloromethane was concentrated to give the title compound of Step B (0.38 g) as a light brown oil.

Provenance & Evidence