3844. 5-Ethyl-2-picoline

Nomenclature

CAS number: 104-90-5
5-Ethyl-2-methylpyridine; aldehyde-collidine; aldehydine; 2-methyl-5-ethylpyridine; 5-ethyl-α-picoline; 3-ethyl-6-methylpyridine.
C8H11N; mol wt 121.18.
C 79.29%, H 9.15%, N 11.56%.

Description and references

Prepd by heating acetaldehyde ammonia in a double vol of abs alc: Ador, Bayer, Ann. 155, 297 (1870); by heating ammonia water and paraldehyde in presence of ammonium acetate: Dürkopf, Schlaugk, Ber. 21, 294 (1888); DE 347820; DE 349184; DE 349267; H. Maier-Bode, J. Altpeter, Das Pyridin und Seine Derivate (Halle, 1934) p 56; Frank et al., J. Am. Chem. Soc. 68, 1368 (1946); Dunn, US 2717897 (1955 to UCC); R. L. Frank et al., Org. Synth. coll. vol. IV, 451 (1963). Continuous process: Takeba et al., US 2935513 (1960 to Takeda).

Chemical structure

Properties

Liquid. Aromatic odor. d423 0.9184. bp747 177.8°; bp20 74-75°; bp17 65-66°. nD20 1.4971. Volatile with steam. Practically insol in water. Sol in alcohol, ether, benzene, dil acids, concd H2SO4.

Derivative

Hydrochloride.
C8H11N.HCl; mol wt 157.64.
C 60.95%, H 7.67%, N 8.89%, Cl 22.49%.

Properties

Hygroscopic needles, freely sol in water.