Water → [3-Methyl-4-(methylsulfanyl)phenyl]methanamine

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Reaction Steps

A solution of lithium aluminium hydride (1.0 M in THF, 18.4 mL, 18.4 mmol) is cooled in an ice bath and treated slowly with a solution of 3-methyl-4-methylsulfanyl-benzonitrile (preparation 66a, 1.0 g, 6.1 mmol) in THF (10 mL) while the temperature is kept below 5° C. The mixture is allowed to warm to room temperature and stirred over night. The mixture is cooled again at 0° C., and water (2 mL) and aqueous sodium hydroxide (4 M, 2 mL) is added. The mixture is filtered and the filtrate is extracted twice with dichloromethane. The combined organic layers are concentrated under reduced pressure. Yield: 923 mg (90% of theory); ESI mass spectrum: [M+H−NH3]+=151; r.t. HPLC: 0.61 min (X011_S03).

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