Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 135409376, compound

Participants

Reaction Steps

To a solution of the product from Step G (0.74 g, 2.2 mmol) in ethanol under a nitrogen atmosphere at room temperature was added Pd/C (10%, 0.10 g) followed by ammonium formate (0.54 g, 8.5 mmol). This suspension was stirred for 24 h at room temperature followed by filtration through a filter-aide. The filtrate was evaporated to a residue that was purified by column chromatography (silica, 5% to 20% gradient of methanol in dichloromethane) to give a solid that was converted to the dihydrochloride salt, which was crystallized from methanol/ether (0.38 g, 58%): m.p 286-288° C.; MS (ES) m/z 232 (M+); 1H NMR (DMSO-d6) δ 8.28 (3H, brs), 6.59 (1H, s), 6.43 (1H, s), 4.40-4.22 (2H, m), 3.61 (11H, m), 2.79 (4H, m), 2.27 (2H, m), 1.18 (3H, d, J=8.0 Hz).

Provenance & Evidence