Acetic Acid → HCID 57559705, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 3-amino-4-methylbenzoic acid (5.00 g, 33.1 mmol), ethyl orthoformate (5.94 mL), ethyl nitroacetate (3.67 mL), and acetic acid (0.2 mL) was heated to 100° C. with stirring for 3.5 h. The mixture was cooled to 85° C. and an additional 66 mL each of ethyl orthoformate and acetic acid were added followed by 5.54 g (99.2 mmol) of iron powder. The mixture was heated to reflux and stirred for 1 h, when an additional 5.54 g of iron powder was added in three portions, each portion after 1 h of stirring at reflux. The mixture was then heated for an additional 6 h before being cooled to room temperature. The mixture was filtered and the solids were washed with EtOAc. The filtrate was collected and concentrated to afford a brown semisolid. The solid was triturated with Et2O/EtOAc to provide 1.93 g (7.04 mmol, 21.3%) of 1-(5-carboxy-2-methyl-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester as a tan solid.

Provenance & Evidence