反应详情

A solution of 3-ethyl-6-methyl(pyridin-2-yl)amine (also see Reimlinger, H. et al. Chem. Ber., 109, 118-124 (1976); Sawyer, J. R. H.; Wibberley, D. G. J. Chem. Soc (Perkin 1), 113801143 (1973); Childs, R. F.; Johnson, A. W. Chem. Ind. (London), 542 (1964)) (41.2 g, 0.4 mol) in sulfuric acid (817 mL) is chilled in an ice bath. To this solution is added a solution of sodium nitrite (23.81 g, 0.345 mol) in H2O (200 mL). The resulting mixture is stirred at ambient temperature for 20 hr. The mixture is brought to pH 9.0 by addition of 3N sodium hydroxide (370 mL) and extracted with ethyl acetate (9×200 mL). The combined organic extract is washed with brine (300 mL), dried, filtered and concentrated. The residue is crystallized from heptane (300 mL) to afford 3-ethyl-6-methyl-1H-pyridin-2-one (also disclosed by Mistryukov, E. A. et al. Izv. Akad. Nauk SSR 512-519 (1964); Chem. Abstr. 64, 90713) (35.78 g, 87% yield) as a white, crystalline solid. The resulting product exhibited characteristic 1H NMR spectrum consistent with that reported in the literature.

1. extractionextracted with ethyl acetate (9×200 mL)
2. extractionThe combined organic extract
3. washis washed with brine (300 mL)
4. customdried
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue is crystallized from heptane (300 mL)