ethyl 2-fluoro-3-oxo-3-phenylpropanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Refluxing of ethyl α-fluorobenzoylacetate (2.25 g, 10 mmol) with o-phenylenediamine (10 mmol) in the mixture of acetic acid and ethanol (25%) for 5 h gave 3-fluoro-1,5-benzodiazepin-2-one derivatives in good yields as follows. ##STR17## wherein X=H, 4-Me, 4-Cl or NO2. It is clear that the first step of this reaction is condensation of carbonyl ketone and amine by losing water and second step is cyclization of their ester with another amine by losing ethanol. When used p-CH3 or p-Cl o-phenylenediamine, these were condensed with α-fluorobenzoylacetate,

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.0 g of ethyl a-fluorobenzoylacetate and 7.0 g of ammonium acetate were added to 50 ml of ethanol, followed by dropwise addition of 6.0 g of acetic acid to this solution with stirring at room temperature. The mixed solution was further stirred under reflux for 4 hours and added to a cooled aqueous solution of sodium hydrogencarbonte. This aqueous mixture was extracted with 200 ml of diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then the solvent was distilled away under reduced pressure to obtain 5.5 g of ethyl 2-fluoro-3-amino-3-phenyl-2-propenoate. The mixed solution was further stirred under reflux for 4 hours This aqueous mixture was extracted with 200 ml of diethyl ether the organic layer was washed with a sodium chloride aqueous solution dried over anhydrous sodium sulfate Then the solvent was distilled away under reduced pressure