Ammonium Chloride → 5-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-chloro-1-methyl-5-nitropyridin-2(1H)-one (Step 5.1) (10.38 g, 55.0 mmol), EtOH (200 mL) and NH4Cl (79 mL, 550 mmol) was added iron (9.22 g, 165 mmol). The reaction mixture was stirred for 1 hr at 85° C., filtered through a pad of celite, and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 2-10%) to afford the title product (6.77 g, 42.7 mmol, 78% yield) as a black solid. tR: 0.29 min (LC-MS 1); ESI-MS: 159 [M+H]+ (LC-MS 1); Rf=0.28 (CH2Cl2/MeOH 9:1).

Provenance & Evidence