Water → HCID 66611737, compound

Participants

Reaction Steps

A boron tribromide solution in dichloromethane (1.0 M, 14.5 ml, 14.5 mmol) was slowly added dropwise with ice-bath cooling in a dry nitrogen atmosphere to a solution of 4-(8-benzyloxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)-3-fluorobenzonitrile (1.45 g, 3.19 mmol) in trifluoroacetic acid (29 ml). When the addition was complete, the mixture were subsequently stirred for a further 30 min. When the reaction was complete (HPLC-MS check), the reaction mixture was carefully added to water (700 ml) and extracted twice with ethyl acetate (290 ml each time). The combined organic phases were washed with water (100 ml) and semi-saturated NaHCO3 solution (150 ml), subsequently dried using Na2SO4 and filtered with suction. The filtrate was evaporated in vacuo, and the residue was chromatographed over flash silica gel (solvent gradient ethyl acetate/0-33% by vol. of ethanol), giving 3-fluoro-4-(8-hydroxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile (1.10 g, 3.03 mmol), as solid. MS: 365.1 (M+H+), TLC (HPTLC): Rf=0.46 (ethyl acetate/ethanol 2:1, parts by volume).

Provenance & Evidence