3-(Dimethylamino)-1-propanol → 3-Dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

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Reaction Steps

Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1 g, Example 33b) with thionyl chloride (10 ml) followed by 3-dimethylamino- 1-propanol (1.1 ml) as described in Example 33c gave 3-dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.52 g). δ (360 MHz, DMSO-d6) 1.93 (2H, m, CO2CH2CH2), 2.20 (6H, s, (CH3)2), 2.44 (2H, t, CH2N), 4.40 (2H, t, CO2CH2), 5.50 (2H s, OCH2), 7.34 (3H, m, m,p-ArH), 7.58 (2H, d, 2 ArH), 7.72 (1H, s, 3-H), 7.88 (1H, d, 6-H) and 8.14 (1H, d, 8-H).

Provenance & Evidence