3-Cyanopyridine → 2,4-difluoro-N-(pyridin-3-ylmethyl)aniline

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A mixture of 3-cyanopyridine (10.4 g), 2,4-difluoroaniline (129.1 g) and a 5% rhodium on carbon catalyst (1.0 g) was treated with hydrogen at 60 psig and 25-30 deg C. until two equivalents of hydrogen had reacted. The hydrogen pressure was incrementally increased to 400 psig during the course of the reaction. After cooling, venting and pursing with nitrogen, the catalyst was removed by filtration. The filtrate analyzed and found to contain 10.4 g of N-(2,4-diflourophenyl)-N-(3-pyridylmethyl)amine which could be isolated by distillation (158-164 deg. C. @ 3 mm Hg) and recrystallization (cyclohexane) to give a white solid with a melting point of 88.5-90 deg C.

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