Water → HCID 178514389, compound

Participants

Reaction Steps

A solution of 3-aminobenzoic acid (41.1 g) in dioxane (300 ml) was treated with 3,5-dimethyl(pyrazole-1-carboxamidine) HNO3 (100 g), DIEA (90 ml) and H2O (100 ml). The reaction was refluxed for 3 hours and stirred overnight at room temperature. The solid was filtered and washed with dioxane (150 ml) and 1:1 dioxane:H2O (250 ml). The solid was then suspended in diethyl ether (400 ml) and CH3CN (100 ml) and treated with 4N HCl/dioxane (100 ml) and 20% HCl (1 ml). After 48 hours, the reaction was filtered and dried to give 3-[(aminoiminomethyl)amino]benzoic acid (34.1 g) as a lavender solid. MS was consistent with the desired product.

Provenance & Evidence