HCID 178512769, compound → HCID 178512767, compound

Participants

Reaction Steps

4-Nitrobenzylguanidine sulfate (0.243 g, 1.0 mmol) was dissolved in water (50 ml) by gentle warming and then cooled to ambient temperature. Activated Raney-Nickel catalyst (Wet form, Aldrich Chemical Co.) (500 mg) was added and the mixture was hydrogenated at 50 p.s.i. for 90 min. The catalyst was filtered and washed with water. To the clear, colorless filtrate was added 2N H2SO4 to pH 1.5. The solution was concentrated to approximately 25 ml; 95% ethanol (150 ml) was added and the solution stored at 4° C. overnight. The colorless needles were filtered and recrystallized from 1N H2SO4 (8 ml) to give stout prisms (0.205 g, 78%), m.p. 248°-250° C. (dec); IR (cm-1) Nujol 3395 (NH), 3260 (NH), 1675 and 1655 (C=N), 1060 (S=O) 835 (1,4 disubstituted benzene); PMR (DMSO-d6) 7.52 (t, 1H, J=5 Hz, CH2NH--), 6.90 (m, 7H) 6.40 (d, 2H, J=8.5 Hz) and 3.98 (d, 2H, J=5 Hz, CH2NH). Anal. calcd. for C8H12N4.H2SO4 : C, 36.64; H, 5.34; N, 21.37. Found: C, 36.70; H, 5.30; N, 21.39.

Provenance & Evidence