Hydrochloric Acid → Diethyl 2-phenyl-2-(5-nitropyridin-2-yl)malonate

HRID 1059381Notes

Reaction equation

[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1.Cl>CN(C)C=O>[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=2)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

14.9 g of diethyl phenylmalonate was dissolved in 50 ml of N,N-dimethylformamide and 2.52 g of sodium hydride (60% oily) was added thereto at room temperature. Next, 5.0 g of 2-chloro-5-nitropyridine was added thereto and the resulting mixture was stirred at 80° C. for 2 hours. After the completion of the reaction, the reaction mixture was poured into ice-water/ethyl acetate and neutralized with dilute hydrochloric acid. After extracting with ethyl acetate, the extract was dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 16.55 g of the title compound as a reddish brown oily substance.

Workup

customat room temperature
customAfter the completion of the reaction
extractionAfter extracting with ethyl acetate
dry with materialthe extract was dried over anhydrous sodium sulfate
filtrationfiltered
distillationThe filtrate was distilled under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-b4abce1a8c80412dbd5100db904a7877
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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