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

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Reaction Steps

The product of example 1b above, 2-phenoxy-6-(phenylamino)benzonitrile, (0.4 g, 1.4 mmol) was dissolved in dry tetrahydrofuran (20 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.28 g, 7.0 mmol) was added in portions over 10 minutes. The reaction mixture was heated to 60° C. for 1 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 0–3% methanol in methylene chloride gave the title compound as a white amorphous solid. ES (+) MS m/e=274 (M−NH3)+.

Provenance & Evidence