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

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).

1. temperaturethe solution was heated at 70° C. overnight
2. temperatureThe reaction mixture was cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in CHCl3 (200 mL)
5. additiontreated with solid Na2CO3 (100 g)
6. waitAfter 1 hour
7. customthe supernatant was decanted
8. washthe residue was washed with warm CHCl3 (3×200 mL)
9. filtrationThe combined supernatants were filtered
10. concentrationconcentrated

ORD record

ord-ea4af3c8240b46bdad146b083ce90f24

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778967B2