Ethyl Acetoacetate → HCID 69285281, compound

Participants

Reaction Steps

20 g (156 mmol) of 4-fluor-3-nitro-aniline, 18.9 ml (134 mmol) of ethyl acetoacetate in cyclohexene (35 ml) were treated with p-toluene sulfonic acid monohydrate (0.24 g) and heated for 9 h at reflux under a water separator funnel. The solvent was removed in vacuo, the residue applied to silica gel column with AcOEt/n-hexane (1:1)) as eluent. Combination of the purified fractions and concentration in vacuo gave 4.3 g (12.5%) of the 3-(4-fluoro-3-nitro-phenylamino)-but-2-enoic acid ethyl ester as yellow crystals. ISN mass spectrum, m/e: 267.2 (M−1 calculated for C12H13FN2O4: 267).

Provenance & Evidence