Ammonium formate → HCID 131734964, compound

Temperature

65 °C

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.

1. customReaction
2. concentrationThe reaction mixture was then concentrated under reduced pressure to a minimal working volume
3. customThe mixture was partitioned between cold water (200 mL) and EtOAc (200 mL)
4. customThe organic phase was separated
5. washwashed with saturated aqueous NaHCO3 (100 mL) and brine (3×100 mL)
6. dry with materialThe organics were dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-96fa88a0bffc4aefb32844439f98b8be

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278917B2