Hydrochloric Acid → HCID 178425541, compound

Participants

Reaction Steps

A mixture of N-cyano-N-methyl-3-toluidine (0.47 g, 3.22 mmol) and 1-naphthylamine.HCl (0.54 g, 3 mmol) in a 5 ml round bottom flask was heated in a preheated oil bath at 170-190° C. for 3 h under N2. The dark brown solution was allowed to cool to room temperature, and it became a rocky solid. The crude product was flash chromatographed on silica gel to yield N-(1-naphthyl)-N′-(m-tolyl)-N′-methylguanidine.HCl (40% yield) as a white powder. Elemental analysis: IR (CH2Cl2): 1625, 1600, 1560 cm−1. 1NMR (CDCl3): δ 2.135 (s, 3H), 3.536 (s, 3H), 6.847-7.972 (m, 11H). 13C-NMR (CDCl3): 20.9, 41.0, 122.6-141.6, 155.8. C19H20N3OCl.1/256 H2O. (Cacl.) C: 70.02%, H: 6.19%, N: 12.89%; (Found) C: 70.33%, H: 6.20%, N: 12.90%

Provenance & Evidence