Reaktion #2045069

Reaktionsgleichung

5-Amino-8-hydroxy-2-methylquinoline

sodium azide

sodium nitrite

→

13

Ausbeute 66.0%

5-Azido-8-hydroxy-2-methylquinoline

Ausbeute 66.0%

Lösungsmittel

hydrochloric acid

water

water

water

Reaktionsbedingungen

Aufarbeitung

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
   Temperaturto warm to room temperature over 24 h in the dark
4. 4
   ExtraktionIsolation by extraction with diethyl ether
5. 5
   Sonstigegave a dark brown solid, which
6. 6
   Sonstigewas recrystallized from light petroleum

Vorschrift

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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