Triethylamine → 4-[(3-Nitroquinolin-4-yl)amino]butan-1-ol

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-hydroxy-3-nitroquinoline (Gerster et al. J Med Chem 2005, 48, 3481) in DMF (0.7 M) was treated dropwise with POCl3 (1.2 eq) and stirred at 50° C. for 30 min. The reaction mixture was poured into ice-water and extracted twice with CH2Cl2. The combined organic layers were washed with water, dried (Na2SO4) and concentrated. The crude product obtained was added to a solution of 4-amino-butanol (1.3 eq) and triethylamine (1.9 eq) in EtOH and heated to reflux for 15 min. After concentration, flash chromatography on silica gel (gradient elution, 2→4% MeOH—CHCl3) afforded 4-(4-hydroxybutyl)amino-3-nitroquinoline as a yellow solid in 97% yield.

Provenance & Evidence