Hydrochloric Acid → HCID 9970997, compound

Participants

Reaction Steps

A mixture consisting of 978 mg (2.84 mmol) of 7, 100 mg 5% Pd/C, and 100 mL of methanol was shaken under 50 psi of H2 for 4 hours. Upon completing the reduction, 10 mL of concentrated hydrochloric acid was added to the reaction mixture with stirring. After filtering the solution through CELITE and washing the filtrate with methanol, the solvent was removed in vacuo and the residue dried for several hours. The dihydrochloride salt of 9 was recrystallized by dissolution in a minimum amount of hot methanol followed by cooling and then addition of ethyl acetate: 893 mg (88%) yield; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.44; 1H NMR (dimethyl-d6 sulfoxide) δ8.40 (2H, brs, 3- and 6-carbamyl proton), 3.64 (6H, s, methoxys), 2.81 (6H, d, J=4.0 Hz, 3- and 6-carbamyl methyls); mass spectrum (EI mode), m/z 282 (P+).

Provenance & Evidence