Ammonium formate → HCID 131734964, compound

Participants

Reaction Conditions

Reaction Steps

A ˜1:1 mixture of ethyl 2-(4-chlorophenyl)-3-oxopropanoate/ethyl 2-(4-chlorophenyl)-3-hydroxyacrylate (50.0 g, 0.22 mol, 1.0 equiv) and ammonium formate (69.6 g, 1.10 mol, 5.0 equiv) in EtOH (500 mL, 10 vol) was heated at 65° C. for 8 h. Reaction was monitored by HPLC (IPC by LCMS (m/z): [M]+ shows 225.9). The reaction mixture was then concentrated under reduced pressure to a minimal working volume. The mixture was partitioned between cold water (200 mL) and EtOAc (200 mL). The organic phase was separated and washed with saturated aqueous NaHCO3 (100 mL) and brine (3×100 mL). The organics were dried over anhydrous Na2SO4, filtered and concentrated to give crude product ethyl 3-amino-2-(4-chlorophenyl)acrylate (42 g, 85% yield) as an unassigned mixture of E/Z isomers (˜1:1) and brown oil. The crude product was used directly for next step without further purification.

Provenance & Evidence