反应详情

A solution of sodium nitrite (4.75 g, 0.07 mol) in water (63 mL) was added dropwise to a stirred solution of anthranilic acid (10 g, 0.07 mol) in concentrated HCl (125 mL) and water (125 mL), maintaining the temperature below 5° C. After addition the mixture was stirred for 10 min then rapidly filtered. The solution was transferred to a dropping funnel and added dropwise to a solution of NaN3 (4.2 g, 0.065 mol) and sodium acetate trihydrate (105 g, 0.77 mol) in water (125 mL). After addition the mixture was stirred at 0° C. for 15 min then at room temperature for 35 min. The suspension was filtered and washed with water. The solid was then dissolved in EtOAc, dried (MgSO4) and the solvent evaporated. The title compound (52 g, 49%) was isolated as a cream solid. 1H NMR (360 MHz, CDCl3) δ 7.24–7.29 (2H, m), 7.62 (1H, d of t, J=8.1 and 1.5 Hz), 8.12 (1H, d of d, J=7.7, and 1.6 Hz).

1. temperaturemaintaining the temperature below 5° C
2. additionAfter addition the mixture
3. filtrationthen rapidly filtered
4. customThe solution was transferred to a dropping funnel
5. additionAfter addition the mixture
6. stirringwas stirred at 0° C. for 15 min
7. waitat room temperature for 35 min
8. filtrationThe suspension was filtered
9. washwashed with water
10. dissolutionThe solid was then dissolved in EtOAc
11. dry with materialdried (MgSO4)
12. customthe solvent evaporated