Methanol → HCID 58345215, compound

Participants

Reaction Conditions

Reaction Steps

3-nitro-N-phenylpyridin-2-amine was dissolved in dimethylsulfoxide (4 mL) and methanol (2 mL) in a round bottom flask. 2-aminonicotinaldehyde 4 (77 mg, 1.1 eq.) was added and Na2S2O4 (274 mg). The reaction mixture was heated to 100° C. for 18 hours. After cooling to room temperature the reaction mixture was diluted with dichloromethane (50 mL) and washed with water and brine. The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate/hexanes) to afford 20 mg of desired product. 400 M Hz 1H NMR (DMSO-d6) δ: 8.29 (dd, J=1.6 Hz and 5.0 Hz, 1H), 8.17 (dd, J=1.1 Hz and 7.8 Hz, 1H), 7.96 (dd, J=1.6 Hz and 4.7 Hz, 1H), 7.35 (dd, J=5.09 Hz and 8.21 Hz, 1H), 7.31-7.26 (m, 4H), 7.18 (dd, J=1.9 Hz and 7.8 Hz, 1H), 6.96 (s, 2H), 6.37 (dd, J=4.6 Hz and 7.8 Hz, 1H), 2.36 (s, 3H); LCMS [M+H]: 302.

Provenance & Evidence