Reacción #612551

Ecuación de reacción

Dowtherm A

5-(((5-fluoropyridin-3-yl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

EtOAc

→

7-fluoro-1,5-naphthyridin-4-ol

Disolventes

—

petroleum ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of reaction
2. 2
   Otroto obtain a grey precipitate
3. 3
   Filtraciónfiltered
4. 4
   Lavadowashed with diethyl ether
5. 5
   Otrodried under vacuum

Procedimiento

To a stirred solution of Dowtherm A at 250° C., was added 5-(((5-fluoropyridin-3-yl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1 g, 0.003 mol) portionwise over a period of 10 minutes. The reaction was monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether, uv active). After completion of reaction, the mixture was cooled to ambient temperature and treated with diethyl ether to obtain a grey precipitate. The precipitate was stirred for 5-10 minutes and filtered, washed with diethyl ether and dried under vacuum to obtain 7-fluoro-1,5-naphthyridin-4-ol as a tan colored solid, (0.4 g, 64.93%). 1H NMR (400 MHz, DMSO-d6): δ 12.68 (bs, 1H), 9.43 (s, 1H), 8.75 (t, J=6.4 Hz, 1H), 8.59 (d, J=8, 1H), 6.99 (d, J=17.2 Hz, 1H). m/z (ESI) 165.1 (M+H)+.

Fuente