1,1,1-Trimethoxybutane → HCID 69507145, compound

Participants

Reaction Steps

A modification of the general method of Part B of Example 6 was followed using 7-bromo-N4-(4,4-dimethoxybutyl)quinoline-3,4 diamine (59.3 g, 167.39 mmol) in lieu of N4-(4,4-diethoxybutyl)quinoline-2,4 diamine. The reaction was incomplete after running overnight. Trimethyl orthobutyrate (5 mL) was added to the reaction mixture and heated to reflux for an additional 2 hours, upon which an additional amount of trimethyl orthobutyrate (5 mL) and pyridinium tosylate (5 mL) were added. After 2 hours of heating to reflux, the mixture was concentrated under reduced pressure, diluted in dichloromethane (300 mL) and methanol (45 mL), washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and the mixture was concentrated under reduced pressure to afford 57.0 g of 7-bromo-1-(4,4-dimethoxybutyl)-2-propyl-1H-imidazo[4,5-c]quinoline as a brown solid.

Provenance & Evidence