Water → Benzenemethanamine, 3-chloro-4-methyl-

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Reaction Steps

15 ml solution of 2.0 g 3-chloro-4-methylbenzonitrile in tetrahydrofuran was added dropwise into 40 ml solution of 453 mg lithium aluminum hydride in tetrahydrofuran in a nitrogen atmosphere. The mixture was heated under reflux for 2 hr and 10 min. The mixture was ice-cooled, and 0.45 ml water, 0.45 ml of 15% aqueous sodium hydroxide, and 1.35 ml water were added dropwise thereinto such that the solution was kept at 10° C. or less. The solution was filtered through Celite, and the resulting filtrate was dried by adding anhydrous sodium sulfate. It was filtered through a NH-form silica gel, and the filtrate was evaporated to give 1.74 g of 3-chloro-4-methylbenzylamine.

Provenance & Evidence