6-Ethylsulfanyl-5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester → 5-Fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester

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Reaction Steps

Freshly activated raney nickel (50 g) was added to a solution of 6-ethylsulfanyl-5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester (67) (31 g, 85 mmol) in anhydrous ethanol and refluxed for 48 h. The solution was cooled and filtered through celite. The filtrate was evaporated under reduced pressure to yield 24 g (93%) of 5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester (68) as a viscous oil which solidified to a white solids after keeping several days under vacuum at room temperature. Mp 90° C. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.2 Hz, 3H), 3.71 (s, 3H), 4.29 q, J=7.2 Hz, 2H), 4.55 (d, J=5.6 Hz, 2H), 6.87 (m, 2H), 7.26 (m, 2H), 7.96 (dd, J=3.2, 8.8 Hz, 1H), 8.12 (m, 1H), 8.35 (d, J=3.2 Hz, 1H); EIMS m/z 305 (M+1).

Provenance & Evidence