1,3-Propanediamine → HCID 57718193, compound

Participants

Reaction Steps

2-amino-5-bromo-isonicotinic acid methyl ester (1.79 g, 7.75 mmol) was added to a stirred mixture of copper iodide (145 mg, 0.76 mmol), sodium iodide (2.36 g, 15.73 mmol) and 1,3-diaminopropane (0.13 ml, 1.55 mmol) in n-pentanol (20 ml) and heated to reflux overnight. The reaction was cooled to room temperature, ethyl acetate (100 ml) added and washed with NaHCO3 solution (50 ml) and brine (50 ml) before being dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 1/4 hexane as eluent to afford 2-amino-5-iodo-isonicotinic acid pentyl ester as a yellow solid (1.51 g, 58%). 1H NMR (CDCl3): 8.36 (1H, s, py); 6.77 (1H, s, py); 4.50 (2H, br s, NH2); 4.24 (2H, t, OCH2); 1.72 (2H, m, OCH2CH2); 1.32 (4H, m, OCH2CH2CH2CH2CH3); 0.81 (3H, t, CH2CH3).

Provenance & Evidence