反应 #2045069

反应方程式

5-Amino-8-hydroxy-2-methylquinoline

sodium azide

sodium nitrite

→

13

收率 66.0%

5-Azido-8-hydroxy-2-methylquinoline

收率 66.0%

溶剂

hydrochloric acid

water

water

water

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred for 20 min
2. 2
   workup.STIRRINGstirred at 0° C. for a further 1.5 h
3. 3
   温度to warm to room temperature over 24 h in the dark
4. 4
   萃取Isolation by extraction with diethyl ether
5. 5
   其他gave a dark brown solid, which
6. 6
   其他was recrystallized from light petroleum

实验过程

5-Amino-8-hydroxy-2-methylquinoline (12; 723 mg, 4.2 mmol) was dissolved in a solution of concentrated hydrochloric acid (0.4 mL) and water (5 mL), cooled to −3° C. in a salt-ice bath, stirred for 10 min, then treated dropwise with a cold solution of sodium nitrite (0.50 g, 7.2 mmol) in water (5 mL). The mixture was stirred for 20 min, then treated dropwise with sodium azide (0.60 g, 9.2 mmol) in water (40 mL), stirred at 0° C. for a further 1.5 h, then allowed to warm to room temperature over 24 h in the dark. Isolation by extraction with diethyl ether gave a dark brown solid, which was recrystallized from light petroleum to yield 13 as light brown crystals (554 mg, 66%). 1H NMR (500 MHz, CD3OD) δ ppm: 3.31 (s, 3H), 7.06 (d, J=8.5 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.36 (d, J=8.5 Hz, 1H), 8.21 (d, J=8.5 Hz, 1H). 13C NMR (125 MHz, CD3OD) δ ppm: 24.9, 111.8, 115.6, 121.6, 123.7, 127.9, 132.6, 139.6, 151.1, 159.7. HRMS (ESI): calcd for C10H8N4O [M+H]+: 201.0771, found: 201.0773.

来源