HCID 71650762, compound → Ethyl 2-amino-8-(pentafluoroethyl)-3H-1-benzazepine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-ethyl 2-(cyanomethyl)-3-(2-nitro-4-(perfluoroethyl)phenyl)acrylate (2.60 g, 6.87 mmol) was added iron powder (2.30 g, 41.2 mmol). The mixture was heated to 90° C. for 5 hours. Upon cooling the acetic acid was removed under vacuum and the resulting semisolid was dissolved in 50% K2CO3 (100 mL) and EtOAc (100 mL). The mixture was filtered to remove insoluble material and the phases were separated. The aqueous phase was extracted with EtOAc (2×100 mL). The combined organics were dried and concentrated. The concentrate was purified via flash chromatography (100% CH2Cl2 to 2% MeOH) to yield (1E,4E)-ethyl 2-amino-8-(perfluoroethyl)-3H-benzo[b]azepine-4-carboxylate (1.8 g, 74%). 1H NMR (CDCl3) δ 1.39 (t, 3H), 2.95 (s, 2H), 4.32 (q, 2H), 5.12 (br s, 1-2H), 7.22-7.27 (m, 2H), 7.47-7.51 (m, 2H), 7.80 (s, 1H).

Provenance & Evidence