反应详情

Glycerol (138.15 g, 1.5 mol) was added dropwise to an ice-cold mixture of "sulfo-mix" (a mixture of nitrobenzene and fuming sulfuric acid, see: Utermohlen, W. P., J. Org. Chem, 1943 8, 544). Addition of 4-aminopyridine (56.46 g, 0.6 mol) was followed by a rapid dropwise addition of water (225 ml), which caused a rise in temperature to 80°; the reaction mixture was allowed to stir until it became homogeneous, and was subsequently heated to 135° for 48 hours. It was then allowed to cool, poured into 1 l ice water, and the pH was adjusted to 13 by the addition of sodium hydroxide pellets. The resulting thick precipitate was removed by filtration, and the filtrate was extracted with methylene chloride (2×2 l). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to yield a crude product, which was purified by column chromatography (98:2 methylene chloride:methanol). The title product was obtained as an amber oil which crystallized upon standing (13.7 g, 0.11 mol, 18% yield).

1. additionmix" (
2. customto 80°
3. temperaturewas subsequently heated to 135° for 48 hours
4. temperatureto cool
5. customThe resulting thick precipitate was removed by filtration
6. extractionthe filtrate was extracted with methylene chloride (2×2 l)
7. dry with materialThe combined organic extracts were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto yield a crude product, which
11. customwas purified by column chromatography (98:2 methylene chloride:methanol)