Реакция #2045069

Уравнение реакции

5-Amino-8-hydroxy-2-methylquinoline

sodium azide

sodium nitrite

→

13

Выход 66.0%

5-Azido-8-hydroxy-2-methylquinoline

Выход 66.0%

Растворители

hydrochloric acid

water

water

water

Условия реакции

Обработка

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
   Температураto warm to room temperature over 24 h in the dark
4. 4
   ЭкстракцияIsolation by extraction with diethyl ether
5. 5
   Другоеgave a dark brown solid, which
6. 6
   Другоеwas recrystallized from light petroleum

Методика

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.

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