Anthranilic Acid → HCID 66753771, compound

Participants

Reaction Steps

Analogously to the method described by Gonsalves et al. (Tetrahedron 1992, 48, 6821) a solution of 3.90 g of ethyl 5,6,7,8-tetrahydro-benzo[1,2,4]triazine-3-carboxylate (Sagi et al., Heterocycles 1989, 29, 2253) is refluxed in 20 ml of dioxane. Then 8.22 g anthranilic acid and 7.02 g isoamyl nitrite, in each case dissolved in 20 ml dioxane, are simultaneously added dropwise within 25 minutes using two dropping funnels. The reaction mixture is refluxed for a further 30 minutes. For working up the cooled dark brown reaction solution is diluted with 150 ml diethyl ether, washed with 100 ml of 2 N sodium hydroxide solution and with water, dried over magnesium sulphate and evaporated down. The brown, oily flask residue is chromatographed through a silica gel column with ethyl acetate/petroleum ether (20:80 to 50:50) as eluant. The product obtained is still somewhat contaminated but is further reacted without any further purification.

Provenance & Evidence