Oxalic Acid → HCID 70279186, compound

Participants

Reaction Steps

A solution of oxalic acid (13.6 mg, 0.151 mmol) in diethyl ether was added dropwise to a stirring solution of 3-methyl-5-(trans-4-hydroxy-1-methyl-2-pyrrolidinyl)-isoxazole (21 e, 25.0 mg, 0.14 mmol) in diethyl ether. After 30 minutes of stirring at ambient temperature, the resulting precipitate was filtered and washed with diethyl ether three times to give, after evaporation of the solvents in vacuo., 26.0 mg of the title compound (21). M.P. 125°-126° C. MS (DCl/NH3) m/e 183 (M+H)+, 200 (M+NH4)+. 1H NMR (D2O) δ: 6.67 (s, 1H, ArH), 5.07-5.17 (m, 1H, OCH), 4.82 (dd, J=10.5 Hz, J=9.9 Hz, 1H, ArCHN), 3.93-4.03 (m, 1H, NCHH), 3.34-3.43 (m, 1H, NCHH), 2.98 (s, 3H, NCH3), 2.66 (ddd, J= 14.4 Hz, J=10.5 Hz, J=4.8 Hz, 1H, OCCHH), 2.55 (dddd, J=14.4 Hz, J=9.9 Hz, J=1.8 Hz, J=1.8 Hz, 1H, OCCHH), 2.33 (s, 3H, ARCH3). Anal. calcd. for C11H16N26lO6 : C, 48.53; H, 5.88; N, 10.29. Found: C, 48.58; H, 5.83; N, 10.04.

Provenance & Evidence