1,1,1-Trimethoxybutane → HCID 57447018, compound

Participants

Reaction Steps

A solution ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (25.15 g, 83.4 mmol, prepared in Part A of Example 8) in toluene (400 mL) was treated with trimethyl orthobutyrate (15.4 mL, 96.2 mmol) and pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) according to, a modification of the method described in Part D of Example 6. The reaction was not complete after five hours and was allowed to cool to ambient temperature overnight. Additional pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) and trimethyl orthobutyrate (2.0 mL, 12 mmol) were added. The reaction was heated at reflux for two hours and then subjected to the work-up procedure to provide 25.0 g of ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Provenance & Evidence