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The hydrochloride salt of 2-propylaniline was prepared by dissolution of a commercial sample of 2-propylaniline in ethyl ether and addition of an ethereal solution of hydrogen chloride until no further precipitate formed. This precipitate was collected by filtration, washed with ether, and dried briefly in vacuo to provide 2-propylaniline hydrochloride, which was used immediately according to the following procedure. A suspension of this material (34.33 g) was prepared in a prechilled solvent mixture of acetic acid (120 ml), water (77 ml), and concentrated hydrochloric acid (43.4 ml), and was held at -12° with efficient stirring. Using strong external cooling as necessary to maintain an internal temperature between -15° and -10°, a solution of sodium nitrite (14.21 g) in water (67 ml) was added over a period of about 20 min. The mixture was then stirred at -18° for 15 min, and was then filtered into a waiting, prechilled (-7°) solution of 2-cyanoacetamide (50.44 g) in water (2.0 liters) containing sodium acetate (266.7 g). There was an immediate color change to deep yellow followed by the formation of a yellow precipitate. The reaction mixture was stirred in a -11° bath for two days. After warming to 10°, the precipitate was collected by filtration, and was washed alternately with hexanes and ice-cold water. After drying at 45° in vacuo over phosphorus pentoxide, there was obtained 42.12 grams (91% yield) of the title compound as a mixture of (E)- and (Z)-isomers.

1. customformed
2. filtrationThis precipitate was collected by filtration
3. washwashed with ether
4. customdried briefly in vacuo