Ethyl Acetoacetate → 3-(4-Ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl ester

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Reaction Steps

A solution of (4-amino-3-iodo-phenyl)acetic acid ethyl ester (9.85 g, 32.3 mmol), ethyl acetoacetate (4.2 g, 32.3 mmol), and toluenesulfonic acid monohydrate (0.3 g, 1.6 mmol) in benzene (150 mL) is refluxed under Dean-Stark conditions overnight. The solution is then cooled to room temperature and washed with sodium bicarbonate (NaHCO3) (2×50 mL) and concentrated in vacuo to give the desired product (12.5 g, 93%). The product is used without further purification in Step 3. MS: 418 (M+1)+.

Provenance & Evidence