Benzoyl Peroxide → HCID 67995475, compound

Participants

Reaction Steps

To a well stirred solution of 2-methoxy-5-methyl-3-nitro-pyridine (8.4 g, 0.05 mol) in carbon tetrachloride (100 mL), benzoyl peroxide (3.5 g, 0.015 mol) and N-bromosuccinimide (17.8 g, 0.1 mol) were added. The reaction mixture was heated at reflux for 48 h under N2 atmosphere. After cooling, the mixture was evaporated. The residue was diluted with saturated aq. Na2CO3 (200 mL) and extracted (3×50 mL CH2Cl2). The combined extracts were washed with brine, dried on MgSO4, and filtered to yield an orange oil-like solid (8.3 g). Purification by chromatography over silica gel eluting with EtOAc/Petroleum ether (0:1 to 1:99 v/v) afforded product as a pale yellow solid. (4.1 g, 43%). 1H-NMR (CDCl3): δ 4.15 (s, 3H, OCH3), 4.51 (s, 2H, CH2), 8.34 (d, 1H, J=2.4 Hz, Py-H), 8.43 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (CDCl3): δ 27.72, 55, 17, 127.18, 133.66, 135.67, 151.40, 156.30.

Provenance & Evidence