反应详情

A solution of ethyl 9-(3-chlorobenzyl)-6-nitro-9H-β-carboline-3-carboxylate (2.7 g, 6.59 mmol) and titanium(III) chloride (36 mL, 20% solution, 46.75 mmol) in a mixture of acetic acid (54 mL), THF (180 mL), water (54 mL) and DMF (10 mL) was stirred for 5 hours at ambient temperature. The reaction mixture was quenched with water (200 mL), and extracted with ethyl acetate (100 mL). The pH of the water layer was adjusted to 7 with saturated Na2CO3 aqueous solution. Then, the resulting precipitate was filtered and dried in vacuo. The product was extracted from the precipitate with CHCl3 in a Soxhlet extractor and purified by chromatography with ethyl acetate to provide the title compound (0.70 g, yield 27.8%). 1H NMR (DMSO-d6): δ 9.06 (s, 1H), 8.70 (s, 1H), 7.50 (d, 1H, J=8.0 Hz), 7.45 (s, 1H), 7.27–7.31 (m, 3H), 7.09 (s, 1H), 7.01 (d, 1H, J=8.0 Hz), 5.75 (s, 2H), 5.05 (s, 2H), 4.36 (q, 2H, J=7.0 Hz), 1.35 (t, 3H, J=7.0 Hz). LCMS (APCI, M+H+): 380.1/382.1=3/1.

1. customThe reaction mixture was quenched with water (200 mL)
2. extractionextracted with ethyl acetate (100 mL)
3. filtrationThen, the resulting precipitate was filtered
4. customdried in vacuo
5. extractionThe product was extracted from the precipitate with CHCl3 in a Soxhlet extractor
6. custompurified by chromatography with ethyl acetate