Hydrogen Bromide → 3-Dimethylaminopropyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide

Participants

Reaction Steps

Treatment of 3-dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.52 g) with hydrogen bromide in acetic acid (10 ml, 48%) as described in Example 33d gave 3-dimethylaminopropyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrobromide (0.27 g), m.p. 228° C. (dec). δ (360 MHz, DMSO-d6) 2.13 (2H, m, CO2CH2CH2), 2.81 (6H, s, (CH3)2) 3.25 (2H, t, CH2N), 4.42 (2H, t, CO2CH2), 6.72 (1H, s, 3-H), 7.45 (1H, d, 6-H), 8.01 (1H, d, 8-H), 9.43 (1H, bs, NH) and 12.04 (1H, bs, NH). (Found: C, 41.60; H, 4.34; N, 6.04%. C15H16Cl2N2O2. HBr.0.4H2O requires C, 41.77; H, 4.16; N, 6.49%).

Provenance & Evidence