5-amino-2-(methylamino)benzohydrazide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure of Sircar, et al., (J. Med. Chem., 24:735-742 (1981)) was followed. A mixture of 5-amino-2-methylaminobenzoic acid hydrazide (35.05 g, 0.194 mol) and 95% diethyl oxalacetate, sodium salt (47.33 g, 0.214 mol, Aldrich Chemical Co.) in 1 L of water was refluxed for 2 hours. The dark solution was cooled to room temperature and sodium carbonate (22.68 g, 0.214 mol) was added. The solution was refluxed for 1 hour, then allowed to cool to room temperature overnight. A small amount of solid formed. The mixture was filtered through a pad of Celite, the filtrate was cooled and acidified by dropwise addition of 10% hydrochloric acid. At a pH of about 4, a solid formed, the mixture was filtered, and the yellow-green solid was washed with water and vacuum-dried to give 29.65 g (59%) of the title compound, mp 249°-252° C., dec. was refluxed for 2 hours The solution was refluxed for 1 hour to cool to room temperature overnight A small amount of solid formed The mixture was filtered through a pad of Celite the filtrate was cooled acidified by dropwise addition of 10% hydrochloric acid At a pH of about 4, a solid formed the mixture was filtered the yellow-green solid was washed with water vacuum-dried