Water → [4-(2-Methylquinolin-4-ylmethoxy)phenyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-chloromethyl-2-methylquinoline (6.84 g, 30.0 mmol), (4-hydroxyphenyl)carbamic acid tert-butyl ester (6.24 g, 30.0 mmol), Cs2CO3 (20.0 g, 60.0 mmol), and n-Bu4NI (11.1 g, 30.0 mmol) in DMSO (150 mL) was stirred at 80° C. for 3 h. The mixture was then cooled, dumped into cold water, and extracted with ethyl acetate. The combined extract was washed with water, brine, dried and concentrated. Chromatograph by CH2Cl2/EtOAc to provide compound [4-(2-methylquinolin-4-ylmethoxy)phenyl]-carbamic acid tert-butyl ester (8.0 g). ESI (M+H)+365.3.

Provenance & Evidence