Methyl 4-nitrobutyrate → HCID 54562479, compound

Participants

Reaction Steps

A mixture of 1.47 g (10 mM) of 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (J. Am. Chem. Soc., 1955, 77, 457-459), 77 mg (10 mM) of ammonium acetate and 2.55 mL (20 mM) of methyl 4-nitrobutyrate (Aldrich) was refluxed in 10 mL of THF for 1 hour. An additional 500 mg of ammonium acetate was added and the mixture refluxed for an additional 3 hours. The reaction was cooled to room temperature, the solvent evaporated, and the residue chromatographed on silica using ethyl acetate as the elutant. Appropriate fractions were combined to yield 410 mg of the desired product as an oil. NMR (D6DMSO) δ12.80 (s, 1H), 8.42 (s, 1H), 8.37 (m, 2H), 8.18 (s, 1H), 7.25 (m, 1H), 3.62 (s, 3H), 3.25 (t, 2H), 2.68 (t, 2H). 13C NMR (D6DMSO) 172.4, 148.7, 144.5, 144.4, 130.0, 127.3, 126.9, 119.9, 117.3, 106.1, 51.6, 30.5, 23.6. Mass Spectrum: m/e=276 (P+1).

Provenance & Evidence