Thionyl Chloride → 2-Dimethylamino-1-methylethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

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Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1.5 g, Example 33b) with thionyl chloride (15 ml) followed by 1-dimethylamino-2-propanol (1.71 ml) as described in Example 33c gave 2-dimethylamino-1-methylethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (1.47 g). δ (360 MHz, DMSO-d6) 1.34 (3H, d, CHCH3), 2.22 (6H, s, N(CH3)2), 2.45 and 2.62 (2H, 2dd, CH2N), 5.29 (1H, m, CO2CH), 5.58 (2H, s, OCH2), 7.41 (3H, m, m,p-ArH), 7.59 (2H, d, 0-ArH), 7.69 (1H, s, 3-H), 7.85 (1H, d, 6-H) and 8.12 (1H, d, 8-H).

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