Methyl Acrylate → Methyl 2-acetamido-3-nitrocinnamate

Participants

Reaction Conditions

Reaction Steps

N-Acetyl-2-bromo-6-nitroaniline, as described above in Step A, (6.3 g, 24.3 mmol), acrylic acid methyl ester (4.4 mL, 48.64 mmol), triethylamine (4.2 mL, 30.4 mmol) and palladium (11) acetate (275 mg, 1.22 mmol) were dissolved in acetonitrile (75 mL) and heated to 75° C. for 18 hours. The cooled reaction mixture was poured into saturated aqueous Na2CO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from MeOH—H2O to yield the above-titled compound.

Provenance & Evidence