Glycerol → 8-Bromo-6-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

4-Amino-3-bromo-benzoic acid (1 eq) and glycerol (2.4 eq) was added to sulfuric acid (6.4M, reaction conc. 0.6M) at 0° C. After 15 min, the bath was removed and 3-nitro-phenylsulfonic acid sodium salt (1.3 eq) was added portionwise. The reaction mixture was heated gradually until exothermic reaction started (between 110-140° C.), the internal temperature was maintained below 170° C. for 1 h. The reaction mixture was cooled to 50° C. and poured slowly into NH4OH-ice (2:1). The title product isolated by filtration, dissolved in warm 5% NH4OH/MeOH and diluted with CH2Cl2. This solution was filtered through silica gel eluting with (NH4OH, MeOH, CH2Cl2, 3:30:70). The residue was stirred in EtOH and the title product isolated by filtration.

Provenance & Evidence