Water → 4-Amino-1-naphthoic acid

Participants

Reaction Steps

4-amino-1-naphthalenecarbonitrile (1.50 g, 8.91 mmol) was dissolved into a 50% KOH solution (18 ml). The heterogeneous solution was heated at reflux for 2-3 days. Once the solution became homogenous and TLC showed no more starting material, the deep red solution was cooled and poured over 200 ml of water. The solution was then filtered and the acid was precipitated with concentrated HCl. The red crystals were filtered and the filtrate was refiltered to give pink crystals. The first fraction was treated with activated carbon to remove some of the red color. 1.51 g (90.6%) of product was obtained. mp 169°-171° C.; 1H NMR (CD3OD) 6.69 (1 H, d, J=8.2 Hz), 7.38-7.43 (1 H, m), 7.48-7.54 (1 H, m), 8.03 (1 H, d, J=8.5 Hz), 8.13 (1 H, d, J=8.2 Hz), 9.09 (1 H, d, J=8.5 Hz); 13C NMR (CD3OD) 107.39, 114.61, 122.99, 123.92, 125.21, 127.40, 128.48, 135.04, 151.35, 171.44; HRMS calc. for C11H7 NO2, 187.0633; found, 187.0642.

Provenance & Evidence