反应详情

Pyridinium tribromide (90% (Aldrich), 9.8 g, 27.6 mmol) was added portion-wise over 10 minutes to a suspension of 5-(1H-indol-4-yl)-nicotinic acid (2.2 g, 9.2 mmol) in 2-methyl-2-propanol (54 mL), ethanol (36 mL) and acetic acid (108 mL). The mixture was stirred at room temperature for 2 hours and then acetic acid (10 mL) was added. After stirring for an additional hour, water (0.5 mL) and zinc dust (6 g, 92 mmol) were added and stirring was continued for another hour. Residual zinc dust was filtered and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (300 mL) overnight. The solid which formed was filtered, washed with water to remove zinc and pyridine salts and dried under high vacuum to give 2.3 g (98%) of 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid.

1. stirringAfter stirring for an additional hour
2. stirringstirring
3. waitwas continued for another hour
4. filtrationResidual zinc dust was filtered
5. washwashed with methanol
6. concentrationThe filtrate was concentrated
7. stirringthe syrupy residue was stirred in water (300 mL) overnight
8. customThe solid which formed
9. filtrationwas filtered
10. washwashed with water
11. customto remove zinc and pyridine salts
12. customdried under high vacuum