1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Hydroxy-4-nitro-benzoic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 2-hydroxy-4-nitrobenzoic acid (5.0 g) in tert-butyl alcohol (100 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.4 g), 1-hydroxybenzotriazole (3.7 g) and triethylamine (7.6 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.3 g).

Provenance & Evidence