反应详情

温度

0 °C

Solid 2-aminonicotinic acid (199 g, 1.44 mole) was added in portions over 4 hr to 1.0 M LiAlH4 in THF (3 L, 3 mole) with stirring under Argon. An ice-bath was applied to control the temperature below 30° C. After the addition was complete, the reaction was heated at reflux for 16 hr, then was cooled to 0° C. and carefully quenched by sequential addition of H2O (120 mL), 15% NaOH in H2O (120 mL), and H2O (350 mL). The resulting thick suspension was stirred for 1 hr, then was filtered through a pad of Celite®. The filter pad was rinsed with THF (1 L), and the filtrate was concentrated to dryness to give the title compound (156 g, 87%) as a pale yellow waxy solid: MS (ES) m/e 125.1 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 7.84 (dd, 1 H), 7.37 (m, 1 H), 6.53 (dd, 1 H), 5.65 (br s, 2 H), 5.16 (t, 1 H), 4.34 (d, J=4.6 Hz, 2 H).

1. customAn ice-bath was applied
2. customthe temperature below 30° C
3. additionAfter the addition
4. temperaturethe reaction was heated
5. temperatureat reflux for 16 hr
6. customcarefully quenched by sequential addition of H2O (120 mL), 15% NaOH in H2O (120 mL), and H2O (350 mL)
7. stirringThe resulting thick suspension was stirred for 1 hr
8. filtrationwas filtered through a pad of Celite®
9. washThe filter pad was rinsed with THF (1 L)
10. concentrationthe filtrate was concentrated to dryness