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C. tert-Butylamine hydrochloride. In a 2-l. flask fitted with an efficient bulb-type reflux condenser are placed 203 g. (1 mole) of tert-butylphthalimide, 1 l. of 95% ethanol, and 59 g. (1 mole) of 85% hydrazine hydrate. The solution is refluxed for 2 hours and cooled, and concentrated hydrochloric acid (about 100 ml.) is added until the solution is strongly acid to Congo red paper, though a large excess of acid is avoided. The voluminous precipitate of phthalhydrazide is collected on a 15-cm. Büchner funnel with the aid of suction and washed with four 100-ml. portions of 95% ethanol. The combined filtrate and washings are concentrated under reduced pressure to a volume of 200 ml. About 1 l. of water is added, any insoluble material is removed by filtration, and the filtrate is concentrated to about 300–350 ml. If any additional insoluble material separates it is removed by filtration, and the solvent is completely removed by evaporation under reduced pressure. This crude amine hydrochloride may be converted to the free amine as described below, or it may be purified by solution in 500 ml. of absolute ethanol, the solution being filtered and 500 ml. of dry ether being added to the filtrate. The crude amine hydrochloride is collected on a filter; the solvent is removed by suction, and the residue is dissolved in hot absolute ethanol using 5 ml. per gram of material; absolute ether (50% of the volume of ethanol) is added, and the solution is cooled in a refrigerator for several hours. All the tert-butylamine hydrochloride is collected on a Büchner funnel and dried in a vacuum desiccator. It weighs 79–97 g. (72–88%) and melts with sublimation at 270–290°.