2-Chloro-3-nitropyridine → HCID 18967512, compound

Participants

Reaction Steps

A mixture of the product from Example 57 (0.338 g, 1.4 mmol), 2-chloro-3-nitropyridine (0.446 g, 2.81 mmol), and 4-dimethylaminopyridine (0.172 g, 1.4 mmol) in dimethylformamide (6 mL) was refluxed 5 hours. The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The organic phase was washed with 1N sodium hydroxide and brine, then it was concentrated onto silica gel and flash chromatographed (1×4 inches silica gel). The elution proceeded as follows: 75% methylene chloride/hexane (175 mL) nil; methylene chloride (250 mL) unweighed excess 2-chloro-3-nitropyridine; 2% methanol/methylene chloride (200 mL) nil, (550 mL) 0.373 g of crude product contaminated with 4-dimethylamino-pyridine. This material was triturated with ether and filtered to give 0.17 g of title product as orange crystals. 1H NMR δ 10.34 (br s, 1 H), 8.59 (dd, J=2, 8.5 Hz, 1 H), 8.54-8.50 (m, 2 H), 7.88 (d, J=9 Hz, 1 H), 7.72-7.70 (m, 1 H), 7.66 (dd, J=2, 9 Hz, 1H), 7.45-7.41 (m, 2 H), 6.89 (dd, J=4.5, 8.5 Hz, 1 H), 3.27 (tt, J=4, 11.5 Hz, 1 H), 3.11 (long range coupled d, J=11.5 Hz, 1 H), 2.41 (s, 3 H), 2.27 (dt, J=2.5, 11.5 Hz, 2 H), 2.09-1.89 (m, 4 H).

Provenance & Evidence