Acetic Anhydride → HCID 11849245, compound

Participants

Reaction Steps

To a solution of 3 (1 mmol) in glacial acetic acid (10 mL) was slowly added acetic anhydride (0.35 mL). After stirring for overnight TLC indicated complete acylation of the starting material, then was added 10% palladium on carbon (80 mg). The mixture was placed on Parr hydrogenation apparatus at 50 psi for 4 h at room temperature. The mixture was filtered through hyflo and the filter pad washed with water. The filtrate was evaporated under reduced pressure and the precipitate was collected and washed with etherto give 5 in 71% yield, mp 236-238° C. 1H NMR (D2O/DMSO-d6); δ 1.78 (s, 2×CH3), 7.31 (d, J=3.6 Hz, 1H), 7.61 (d, J=3.6 Hz, 1H), 7.85-8.11 (m, 8H). EIMS m/e (rel. int.); 304 (M+, 20), 287 (100), 270 (50), 216 (30), 190 (10). High resolution Calc. for C18H16N4O ms 304. 13241. Observed 5 304. 13201. Anal. Calc. for C16H14N4O2-2.0AcOH-1.75H2O-0.25EtOH: C %, 57.81; H %, 6.25; N %, 11.98. Found C %, 58.18; H %, 5.90; N %, 11.56.

Provenance & Evidence