Ethyl 4-azido-7-chloroquinoline-3-carboxylate → 4-Azido-7-chloroquinoline-3-carboxylic acid

Participants

Reaction Steps

Ethyl-4-azido-7-chloroquinoline-3-carboxylate (0.57 g; 0.002 M) in 10% aq. NaOH (10 ml) and stirred at 40° C. for 5 hr. The unreacted ester, m.p. 91°-4° C., was filtered off, the filtrate acidified to pH 3 with 5 M HCl, the product filtered off, washed well with water and dried in vacuo over P2O5. 0.33 g (66%), m.p. 284°-6° C. (dec.), (Found: C, 46.7; H, 2.3; Cl 14.1%. C10H5ClN4O2.1/2H2O requires C, 46.6; H, 2.4; Cl 13.8%), νmax (KBr) 2158, 1705 (br), 1608, 1562, 1395 (br), 1210 and 798 cm-1, δ [(CD3)2SO] 7.72 (m), 8.09 (d), 8.36 (d) and 9.18 (s) (aromatic H's)

Provenance & Evidence