Reaktion #1451693

Reaktionsgleichung

2-bromo-4,6-diaminonicotinonitrile

ethanol

sodium

sodium

→

light orange solid

Ausbeute 65.0%

4,6-Diamino-2-ethoxy-nicotinonitrile

Ausbeute 65.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo a 5 mL sealable heavy walled glass tube suitable for microwave heating
2. 2
   Sonstigehad reacted
3. 3
   workup.ADDITION2,790,806, 1957) was added
4. 4
   SonstigeThe tube was sealed
5. 5
   Temperaturthen cooled
6. 6
   SonstigeThe orange precipitate which formed
7. 7
   Waschenwas washed with water until pH=7
8. 8
   Sonstigedried under reduced pressure at 105° C.

Vorschrift

To a 5 mL sealable heavy walled glass tube suitable for microwave heating containing 5 mL of absolute ethanol was added 150 mg (6.5 mmol) of sodium metal. The mixture was stirred until all of the sodium had reacted, then 1.00 g (4.71 mmol) of 2-bromo-4,6-diaminonicotinonitrile (E. I. du Pont de Nemours and Company U.S. Pat. No. 2,790,806, 1957) was added. The tube was sealed, and the reaction was heated with a microwave apparatus at 150° C. for 10 minutes then cooled and diluted with 15 mL of water. The orange precipitate which formed was washed with water until pH=7, then dried under reduced pressure at 105° C. to provide 0.545 g (65%) of a light orange solid. 1H NMR (300 MHz, d6-DMSO) δ 6.19 (s, 2H), 6.14 (s, 2H), 5.32 (s, 1H), 4.23 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.1 Hz), MS (ES) m/e=151 (M−Et+H)+, 179 (M+H)+.

Quelle