Hydrogen Peroxide → 1-Oxo-6,7,8,9-tetrahydro-5H-1lambda~5~-cyclohepta[b]pyridine

Participants

Reaction Steps

To a stirred solution of 2,3-cycloheptenopyridine (42.94 g, 0.292 mol) in glacial acetic acid (160 mL) at room temperature was added 30% H2O2 (30 mL) and the resultant solution was heated to 70° C. After 6 hours, the reaction mixture was cooled to room temperature, additional H2O2 (30 mL) was added, and the solution was heated at 70° C. overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in CHCl3 (200 mL) and treated with solid Na2CO3 (100 g). After 1 hour, the supernatant was decanted and the residue was washed with warm CHCl3 (3×200 mL). The combined supernatants were filtered and concentrated to provide 60 g of 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine 1-oxide as a yellow oil. 1H NMR (CDCl3) δ 1.63-1.73 (m, 4H), 1.82-1.91 (m, 2H), 2.77-2.83 (m, 2H), 3.36-3.42 (m, 2H), 6.94-7.05 (m, 2H), 8.17,(d, 1H, J=6.1 Hz).

Provenance & Evidence