Ammonium Chloride → 6-Chloro-N2,4-dimethyl-2,3-pyridinediamine

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 6-chloro-N,4-dimethyl-3-nitropyridin-2-amine (Step 109.2) (1 g, 4.96 mmol), Iron (1.385 g, 24.80 mmol) and 7N NH4Cl (21.26 mL, 149 mmol) in EtOH (40 mL) and the resulting mixture was heated up and stirred at 85° C. for 30 min. The reaction was filtered through a pad of Celite and volatils were removed under reduced pressure. The resulting aq. layer was extracted with CH2Cl2, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude paterial was purified by silica gel column chromatography (50% EtOAc/hexane) to afford the title product (660 mg, 3.85 mmol, 78% yield) as beige oil. tR: 0.74 min (LC-MS 2); ESI-MS: 172 [M+H]+ (LC-MS 2); Rf=0.39 (50% EtOAc/hexane); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.98 (s, 3H) 2.77 (d, J=4.7 Hz, 3H) 4.46 (s, 2H) 5.91 (d, J=4.3 Hz, 1H) 6.28 (s, 1H).

Provenance & Evidence