反应详情

5-Nitroanthranilic acid (5.0 g, 27.45 mmol) is dissolved in THF (100 mL) and 1 M borane/THF complex (55 mL, 54.9 mmol) is added. The mixture is heated to reflux for 1 h. Analysis by TLC indicates complete consumption of starting material. The volatiles are removed in vacuo and the residue is dissolved in ethyl acetate (150 mL). The organic phase is washed with 1 N HCl, saturated NaHCO3, and saturated NaCl. Evaporation provides 10.8 g (98%) of a dark brown oil product which is used directly in the next reaction; 1H-NMR (500 MHz, CDCl3); δ 4.61 (s, 2 H), 6.62 (s, 1 H), 8.01 (m, 2 H).

1. addition1 M borane/THF complex (55 mL, 54.9 mmol) is added
2. temperatureThe mixture is heated
3. temperatureto reflux for 1 h
4. customconsumption of starting material
5. customThe volatiles are removed in vacuo
6. dissolutionthe residue is dissolved in ethyl acetate (150 mL)
7. washThe organic phase is washed with 1 N HCl, saturated NaHCO3, and saturated NaCl
8. customEvaporation