Methanol → Methyl 3-(3-aminophenyl)isonicotinate

Participants

Reaction Steps

Into an RBF was placed methyl 3-(3-nitrophenyl)isonicotinate (1.85 g, 7.16 mmol) and to this was added methanol (50 ml), ammonium formate (6.0 g, 35.8 mmol) and 5 wt % Pd/C (Degussa type). No initial exotherm was noticed (to the touch) and no bubbling or gas evolution was observed. After 2 h, some SM was observed to be undissolved and THF (25 ml) was added to aid in solubility. The reaction was slow at room temperature. The reaction mixture was then placed on the Buchi hydrogenator overnight. The mixture was then filtered through a pad of Celite and washed with ethyl acetate. This solution was washed with water, separated and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The orange oil was purified by silica gel flash chromatography using 30% ethyl acetate/Hexanes as eluent to yield 1.15 g (71% th) of an orange oil.

Provenance & Evidence