反应详情

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.

1. temperatureThe heterogeneous solution was heated
2. temperatureat reflux for 2-3 days
3. temperaturethe deep red solution was cooled
4. filtrationThe solution was then filtered
5. customthe acid was precipitated with concentrated HCl
6. filtrationThe red crystals were filtered
7. customto give pink crystals
8. additionThe first fraction was treated with activated carbon
9. customto remove some of the red color