Chlorosuccinimide → 2,3-Dichloro-N-methyl-4-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-N-methyl-isonicotinamide (12-2, 1.19 g, 6.98 mmol) was dissolved in 2 mL anhydrous THF and the solutin was cooled to −78° C. LDA (2M, 7.33 mL, 14.7 mmol) was added dropwise and the reaction turns orange. After 15 min NCS (1.02 g, 7.67 mmol) was added and the reaction was allowed to warm to RT. After 1 h at RT HPLC shows ˜3:1 starting material/product. The reaction was quenched with water, extracted 3× w/EtOAc, and the organic phases were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative reverse phase HPLC to afford the pure titled compound. 1H NMR (CDCl3) δ 8.36 (d, 1H, J=4.8 Hz), 7.41 (d, 1H, J=4.8 Hz), 6.10 (bs, 1H), 3.05 (d, 3H, J=4.9 Hz).

Provenance & Evidence