Sodium Hydroxide → HCID 19792778, compound

Participants

Reaction Steps

A solution of 5-[3-(cyclopentyloxy)-4-methoxyphenyl]-3-oxo-l-pyrazolidinecarboxylic acid methyl ester (0.696 g, 2 mmol) in methanol (4 ml) is mixed with 2.5 N sodium hydroxide solution (1.2 ml, 3 mmol). The reaction mixture is kept at 40° overnight. The solvent is removed, and the residue partitioned between ethyl acetate/water, dried and the solvent evaporated. Residue (0.7 g) is allowed to crystallize over ethyl acetate/ether to yield solid (0.29 g) m.p. 137-139°. A crystallization from ethyl acetate/ether gives analytical sample m.p. 136 NMR (Me2SO-d6); δ 9.38 (1H, broad, NH), 7.02 (1H, d, arom), 6.89 (2H, m, arom), 4.75 (1H, m, carbinolic), 4.27 (1H, q, benzylic), 3.72 (3H, s, 0--CH3), 3.60 (1H, d, --CHCO), 3.37 (1H, d, --CHCO), 3.04 (1H, q, --CHCO), 2.25 (1H, q, --CHCO), 1.88 (2H, m, cyclopentyl --CH), 1.70 (4H, m, cyclopentyl --CH), 1.56 (2H, m, cyclopentyl --CH), IR (KBr), 3210, 2940, 2450, 1710, 1630, 1510 cm-1.

Provenance & Evidence