2,4-Dimethylbenzylamine synthesis

Yield: 100%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran;diethyl ether at 0 - 20; for 3 h;

Steps:

133.a
(2,4-Dimethylphenyl)methanamine: Lithium aluminum hydride 1M solution in THF (15.2 ml, 15.2 mmol) was placed in a pre-dried flask under argon at 0° C.; a solution of 2,4-dimethylbenzonitrile (1.0 g, 7.6 mmol) in 15 ml of anhydrous ether was added drop wisely. After the addition, the reaction mixture was warmed up slowly to r.t. and stirred for 3 hr. then it was cooled to 0° C., anhydrous sodium sulfate was added, and 1 ml of water was added drop wisely. The mixture was diluted with ethyl acetate, the insoluble matter was filtered out, the filtrate was washed with water and brine, dried over MgSO₄, filtered and evaporated to give 1.03 g of pure (2,4-dimethylphenyl)methanamine in quantitative yield without purification.

References:

Tachdjian, Catherine;Patron, Andrew P.;Adamski-Werner, Sara L.;Bakir, Farid;Chen, Qing;Darmohusodo, Vincent;Hobson, Stephen Terrence;Li, Xiaodong;Qi, Ming;Rogers, Daniel Harry;Rinnova, Marketa;Servant, Guy;Tang, Xiao-Qing;Zoller, Mark;Wallace, David;Xing, Amy;Gubernator, Klaus US2005/84506, 2005, A1 Location in patent:Page/Page column 80