3-Pentanamine → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

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Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (prepared as described in Preparation E, 3.4343 g, 10.74 mmol) and 1-ethyl-propyl-amine (10 ml) in 10 ml of DMSO was heated at 120° C. for 15 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow solid. The yellow solid was recrystallized with hexane to give 2.519 g (63%) of the title compound of Preparation F as white crystals, mp 106-107.5° C. Anal. for C22H30N2O3 (C,H,N). 1H NMR (CDCl3) δ 8.04(d,1H), 6.85(s,2H), 6.06(s,1H), 3.85(s,3H), 3.32(m,1H), 2.28(s,3H), 2.10(s,3H), 2.07(s,3H), 1.62(m,4H), 0.95(t,6H) ppm.

Provenance & Evidence