Triethylamine → Methyl 3-pentanamidobenzoate

Participants

Reaction Steps

To a solution of methyl 3-aminobenzoate (6.0 g) and triethylamine (4.5 g) in methylene chloride (90 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (4.8 g). The mixture was stirred for one hour. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water, followed by drying and concentration to dryness. The concentrate was crystallized from ethyl acetate-hexane to afford colorless prisms (8.1 g, 87%), m.p. 101-102° C. 1H-NMR(90 MHz, CDCl3) δ: 0.93(3H,t), 1.2-1.9(4H,m), 2.37(2H,t), 3.90(3H,s), 7.36(1H,t), 7.5(1H,br s), 7.70-7.95(2H,m), 8.03(1H,t).

Provenance & Evidence