O-Toluidine → HCID 13143783, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-3-nitropyridine (4.13 g, 26.1 mmol), o-tolylamine (3.4 mL, 31.3 mmol) and Et3N (4.4 mL, 31.3 mmol) in DMF (10 mL) was stirred at 90° C. for 1 h under a nitrogen atmosphere. Additional o-tolylamine (2 mL, 18.2 mmol) was added and stirring continued for 16 h. The mixture was partitioned between DCM and water. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 20-100% DCM in cyclohexane) to afford the title compound as an orange solid (3.96 g, 66%). LCMS (Method C): RT 3.60 min [M+H]+ 230.3

Provenance & Evidence