3-Hydroxyanthranilic Acid → Anthranilic acid, 3-hydroxy-, methyl ester

Participants

Reaction Steps

A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3-hydroxyanthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16 h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by flash chromatography (gradient: heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR=0.70 min; [M+H]+=168.0.

Provenance & Evidence