Diethyl Oxalate → Ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropanoate

HRID 751628Notes

Reaction equation

[O-]CC.[K+].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[CH3:15][O:16][C:17]1[N:22]=[C:21]([CH3:23])[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=1>C(OCC)C.C(O)C>[CH2:13]([O:12][C:5](=[O:11])[C:6](=[O:8])[CH2:23][C:21]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][CH:18]=[C:17]([O:16][CH3:15])[N:22]=1)[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of potassium ethoxide (0.55 g, 6.55 mmol) in diethyl ether (20 mL, anhydrous) and ethanol (4 mL) was added diethyl oxalate (894 μL, 6.55 mmol) and the reaction mixture was stirred for 30 min prior to the addition of 6-methoxy-2-methyl-3-nitropyridine (Preparation 33, 1.0 g, 5.95 mmol) in diethyl ether (8 mL). The resulting red suspension was stirred at rt, under argon, for 20 h. The mixture was filtered, the solid washed thoroughly with diethyl ether then dried. The red solid was then taken up in hot water and the solution cooled to 0° C. The precipitate was filtered, washed with cold water, and dried to give the title compound as a beige solid. δH (CDCl3): 1.40 (3H, t), 4.07 (3H, s), 4.39 (2H, q), 6.74 (1H, d), 7.57 (1H, s), 8.40 (1H, d), 13.82 (1H, s).

Workup

stirringThe resulting red suspension was stirred at rt, under argon, for 20 h
filtrationThe mixture was filtered
washthe solid washed thoroughly with diethyl ether
customthen dried
filtrationThe precipitate was filtered
washwashed with cold water
customdried

Sources & evidence

ORD record: ord-a4de3c39692d49fe8c4ff464c7f6d4d7
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405210B2

Reaction notes

Loading…