(4-METHYL-BENZYL)-HYDRAZINE HYDROCHLORIDE synthesis

Yield:-

Reaction Conditions:

Stage #1: tert-butyl isopropylidenecarbazate;4-Methylbenzyl bromidewith sodium hydride in acetonitrile at 80;
Stage #2: with hydrogenchloride in ethanol;water;ethyl acetate;

Steps:

169 Example 169

The intermediate (1.76 g) obtained in Step 1 of Example 168, 4-methylbenzylbromide (1.85 g) and sodium hydride (300 mg) are stirred overnight in acetonitrile (30 ml) at 80C. Water is added and the mixture is extracted with ethyl acetate. After drying over sodium sulfate, the solvent is evaporated. The obtained residue is stirred overnight in 4 Mol hydrochloric acid-ethyl acetate solution (10 ml) at room temperature, and the solvent is evaporated. The obtained residue is dissolved in ethanol (20 ml) and conc. hydrochloric-acid (5 ml) is added. The mixture is stirred overnight at room temperature, concentrated to dryness and washed with ethyl acetate to give 4-methylbenzylhydrazine hydrochloride (1.9 g). A compound of Example 169 was synthesized according to a method similar to the method of Example 3 from the obtained hydrazine hydrochloride. MS (ESI) m/z 272(M+H)+

References:

EP1396493,2004,A1 Location in patent:Page 43