1-Pyrrolidineethanol → 2-(1-Pyrrolidinyl)ethyl 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 1-(2-hydroxyethyl) pyrrolidine (0.43 ml) as described in Example 33c, gave 2-(1-pyrrolidinyl)ethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.7 g). δ (360 MHz, DMSOd6) 1.70 (4H, bs, pyrrolidine-3,4-H), 2.60 (4H, bs, pyrrolidine-2.5-H), 2.88 (2H, t, CH2N), 4.48 (2H, t, CO2CH2), 5.50 (2H, s, OCH2), 7.38 (3H, m, m,p-ArH), 7.58 (2H, d, o-ArH), 7.71 (1H, s, 3-H), 7.86 (1H, d, 6-H) and 8.13 (1H, d, 8-H).

Provenance & Evidence