反应详情

To 0.80 g (2.4 mmol) of methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate in 50 mL of tetrahydrofuran at −78° C. was added 7.3 mL (7.3 mmol) of DIBAL (1M in tetrahydrofuran). The mixture was allowed to warm to room temperature and stirred for 6 h. The reaction was quenched with 1N HCl and concentrated to a slurry. The slurry was dissolved in dichloromethane and was concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 4% methanol/dichloromethane mixture to give 0.44 g (60%) of the title compound as a light yellow powder.

1. customThe reaction was quenched with 1N HCl
2. concentrationconcentrated to a slurry
3. dissolutionThe slurry was dissolved in dichloromethane
4. concentrationwas concentrated onto silica gel
5. customThe crude material was purified by flash chromatography
6. washeluting with a 4% methanol/dichloromethane mixture