Aniline → Methyl 4'-(anilinomethyl)biphenyl-2-carboxylate

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Reaction Steps

Phenylamine (56 mg) was added to the compound (120 mg) prepared in Example 4 in methanol solution (3 mL) and stirred for 4 hours at room temperature. The reaction mixture was added to sodium borohydride (37 mg) and stirred for 1.5 hours. To alkalinize, 5 mol/L sodium hydroxide solution was added to the concentrated reaction mixture and then extracted with ethyl acetate. The organic layer was washed with saturated sodium and dried by anhydrous sodium sulfate, and then concentrated to obtain the titled compound (124 mg) having the following physical data by purifying the obtained residue by silica gel column chromatography (diethyl ether:hexane=1:2).

Provenance & Evidence