Sodium Sulfate → 2-Phenoxy-6-(phenylamino)benzylamine

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Reaction Steps

The product of example 1b above, 2-phenoxy-6-(2,6-difluorophenylamino)benzonitrile, (0.34 g, 1.06 mmol) was dissolved in dry tetrahydrofuran (40 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.384 g, 10.1 mmol) was added, and the reaction mixture was heated to 65° C. for 0.5 hour. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate. The solvent was evaporated and the residue triturated with ethyl acetate, filtered and evaporated. Flash chromatography on silica gel eluted with 40% methylene chloride/hexane to which 3% methanol was added followed by Gilson hplc purification gave the title compound as a white amorphous solid. mp 113–116° C.

Provenance & Evidence