Hydrochloric Acid → HCID 178518628, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chloro-4-(2-cyanoethyl)-3-phenyl-quinolin-2(1H)-one (Example 39, 0.45 g) in 1-methyl-2-pyrrolidinone (50 ml) under nitrogen at room temperature, was added sodium azide (0.28 g) followed by triethylamine hydrochloride (0.30 g). The reaction mixture was heated to 150° C. and stirred for 48 h. After allowing to cool, the mixture was poured into water (100 ml), acidified to pH 1 with concentrated HCl and extracted with ethyl acetate (3×75 ml). The combined organic layers were extracted with 1N sodium hydroxide (3×75 ml) and the combined aqueous phases were washed with diethyl ether (2×75 ml), then acidified to pH 1 using concentrated HCl. The aqueous layer was extracted with ethyl acetate (3×75 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was removed in vacuo to leave a solid residue. Recrystallisation from a water/methanol mix then from ethyl acetate gave the title compound (0.05 g). Mp 231°-233° C. Found: C, 61.31; H, 4.20; N, 19.41; C18H14N5OCl. 0.1 H2O requires C, 61.14; H, 4.05; N, 19.81%. δ (360 MHz, DMSO-d6) δ 3.05 (4H, bs, CH2CH2Tet)), 7.10-7.42 (7H, m, Ph+6-H+8-H), 7.86 (1H, d, J=8.73 Hz, 5-H), 12.00 (1H, bs, NH). m/z (CI+), 352, (M+1).

Provenance & Evidence