反应详情

温度

-20 °C

A stirred mixture of 3-hydroxypyridine-2-carboxylic acid (1.39 g, 0.01 mol) in dry THF (60 mL) under argon was cooled to −20° C. To this was added all at once a 20% solution of phosgene in toluene (5.1 g, 0.01 mol) and the resulting mixture was stirred for 90 minutes while the temperature slowly rose to 0° C. The reaction mixture was then recooled to −20° C. and a solution of diisopropylethylamine (2.58 g, 0.02 mol) in THF (20 mL) was added dropwise over 30 minutes. After the addition was complete, the mixture was stirred an additional 2 hours as the temperature was slowly brought to 0° C. Stirring was continued at 0° C. overnight. To this stirred mixture was added, all at once, 2-(4-chlorophenyl)ethylamine (1.56 g, 0.01 mol), and the resulting mixture was stirred at room temperature for 6 hours. The mixture was diluted with ether (100 mL), washed with 1N HCl (100 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (1.95 g). The mass spectrum showed the expected 3:1 parent ion ratio at m/e 276 and 278.

1. customslowly rose to 0° C
2. customwas then recooled to −20° C.
3. additionAfter the addition
4. stirringthe mixture was stirred an additional 2 hours as the temperature
5. customwas slowly brought to 0° C
6. stirringStirring
7. waitwas continued at 0° C. overnight
8. additionTo this stirred mixture was added
9. washwashed with 1N HCl (100 mL)
10. dry with materialdried (MgSO4)
11. concentrationconcentrated