Benzoic acid, 3-amino-, methyl ester → HCID 86760244, compound

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Reaction Steps

A mixture of 5-[2-(adamantan-1-yloxy)-1-hydroxy-ethylidene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (27.27 g, 81.1 mmol), 3-amino-benzoic acid methyl ester (11.68 g, 77.2 mmol) and DMAP (cat.) in benzene (550 mL) was heated at reflux for 2 hours. The mixture was allowed to cool to room temperature. The solvent was removed by evaporation at reduced to give the crude product as a red oil. Purification by flash column chromatography (DCM:ethyl acetate 6:1) yielded the title compound as a yellow foam (20.34 g, 68%). 1H NMR (CDCl3) 9.22 (1H, br s), 8.08-8.07 (1H, t), 7.91-7.88 (1H, m), 7.81-7.77 (1H, m), 7.43-7.38 (1H, m), 4.14 (2H, s), 3.91 (3H, s), 3.74 (2H, s), 2.19 (3H, br s), 1.83-1.58 (12H, m).

Provenance & Evidence