Sodium hydride → 6-Ethoxycarbonylmethoxy-5-nitro-nicotinic acid methyl ester

HRID 723520Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[O:3].[H-].[Na+].[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16](Cl)=[N:15][CH:14]=1>O1CCOCC1>[CH3:10][O:11][C:12](=[O:23])[C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[N:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl glyoxalate (2.80 g) in dry dioxan (100 mL), cooled in ice, was treated with sodium hydride (60% dispersion in oil; 1.30 g) and the mixture was heated at 50° C. for 30 minutes and cooled in ice. A solution of 6-chloro-5-nitro-nicotinic acid methyl ester (5.25 g) [prepared as described by A. H. Berrie et al. J. Chem. Soc. 2590-2594 (1951)] in dioxan (40 mL) was added and the solution was stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was evaporated to dryness, sodium bicarbonate solution was added to pH 7, and the mixture extracted with chloroform, dried (anhydrous sodium sulfate) and evaporated to afford a semi-solid that was chromatographed on silica gel [dichloromethane-hexane (1:1) then dichloromethane] to afford the product (4.70 g).

Workup

temperaturecooled in ice
customat room temperature
customovernight
customThe reaction mixture was evaporated to dryness, sodium bicarbonate solution
additionwas added to pH 7
extractionthe mixture extracted with chloroform
dry with materialdried (anhydrous sodium sulfate)
customevaporated
customto afford a semi-solid
customthat was chromatographed on silica gel [dichloromethane-hexane (1:1)

Sources & evidence

ORD record: ord-f403910b223c4abba388c95e102534bb
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141564B2

Reaction notes

Loading…