反应详情

A solution of 8-nitro-quinoline-7-carbaldehyde (Intermediate 204) (500 mg, 2.4 mmol) and aniline (270 μl, 2.9 mmol) in MeOH (20 ml) under a nitrogen atmosphere was stirred at room temperature for 16 hours. Sodium borohydride (269 mg, 7.1 mmol) was added and stirring continued at room temperature for 1 h. The reaction mixture was concentrated in vacuo and residue was diluted with sat. NaHCO3 solution (30 ml) and was extracted with DCM. The organic phases were dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc gradient elution to give the title compound (0.48 g, 69%).

1. concentrationThe reaction mixture was concentrated in vacuo and residue
2. additionwas diluted with sat. NaHCO3 solution (30 ml)
3. extractionwas extracted with DCM
4. dry with materialThe organic phases were dried (MgSO4)
5. concentrationconcentrated in vacuo
6. customThe crude residue was purified by column chromatography with heptane/EtOAc gradient elution