反应详情

温度

50 °C

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.

1. extractionextracted twice with CH2Cl2
2. washThe combined organic layers were washed with water
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated
5. customThe crude product obtained
6. temperatureheated
7. temperatureto reflux for 15 min
8. concentrationAfter concentration, flash chromatography on silica gel (gradient elution, 2→4% MeOH—CHCl3)