Dimethylformamide → [2-(2-Chloro-5-nitro-pyridin-4-yl)-vinyl]dimethyl-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-4-methyl-5-nitro-pyridine (2 g, 11.59 mmol) in DMF (11.6 mL) was treated with 3.08 mL (23.2 mmol, 2 eq) of DMF-dimethylacetal and the reaction mixture was stirred at 100° C. for 4 h. All volatiles were removed under reduced pressure. Column chromatography (silica, 20% EtOAc/hexanes) provided 2.37 g (90%) of [2-(2-chloro-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine. TLC (silica, 20% EtOAc/hexanes): Rf=0.30. MS (electrospray): exact mass calculated for C9H10ClN3O2, 227.05; m/z found, 228.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.79 (s, 1H), 8.02 (s, 1H), 7.35 (d, J=13 Hz, 1H), 5.94 (d, J-=13 Hz, 1H), 2.96 (s, 3H), 2.87 (s, 3H).

Provenance & Evidence