Picolinic acid → HCID 18689947, compound

Participants

Reaction Steps

A solution of 2,2-dimethyl-1,3-propanediamine (5.00 g, 48.9 mmol) in DMF (500 mL) was treated with picolinic acid (12.6 g, 0.10 mol), 1-hydroxybenzotriazole hydrate (13.9 g, 0.10 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.7 g, 0.10 mol) and iPr2NEt (17.9 mL, 0.10 mol) at room temperature. After 18 h, the reaction mixture was evaporated under vacuum and the residue purified by flash chromatography (75% EtOAc/hexanes, silica gel) to give 13.95 g (91%) the above named product as a clear solid. A fraction of this product (5.63 g) was recrystallized from ethyl acetate/hexane by slow evaporation to give 3.92 g of pure product as white needles. MS (ES+) m/e 313 [M+H+ ].

Provenance & Evidence