Hydrochloric Acid → HCID 19935699, compound

Participants

Reaction Steps

A mixture consisting of 6-hydroxy-α-methyl carbazole-2-acetic acid (2.6 g, 0.010 mol), dimethyl sulfoxide (200 mL), sodium hydroxide (2.0 g in 20 mL H2O, 0.05 mol) and 2-chloromethylquinoline.HCl (4.0 g, 0.018 mol) is heated to 80° C. for 3 hours. The reaction mixture is cooled, poured into water (1000 mL), and the pH is adjusted to 4 with 1N HCl. The aqueous solution is extracted with ethyl acetate (4×300 mL) and the organic layers are combined, washed with water (2×300 mL), once with brine (300 mL), dried over MgSO4, filtered and concentrated to give 3.0 g of crude product. The latter is chromatographed on silica gel using 10% methanol/methylene chloride as an eluent to give 8 g of product, m.p. 197°-199° C.

Provenance & Evidence