Water → Ethyl 2-(3-nitropyridin-2-yl)acetate

HRID 840942Notes

Reaction equation

[N+:1]([C:4]1[C:5]([CH:10](C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O.[Cl-].[Li+]>CS(C)=O.[Cl-].[Na+].O>[N+:1]([C:4]1[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Diethyl (3-nitropyridin-2-yl)-malonate (12.5 g, 0.044 mol) was dissolved in DMSO (150 mL), and water (0.79 mL, 0.044 mol) and lithium chloride (4.65 g, 0.11 mol) were added at room temperature under nitrogen. The reaction was warmed to 100° C. for 12 hours, and more lithium chloride (1 g) was added to the reaction. The reaction was heated for another 5 hours and cooled to room temperature. Brine (150 mL) was added, and the reaction mixture was extracted with EtOAc (3×275 mL). The extracts were combined, dried over sodium sulfate and concentrated in vacuo. The resulting residue was triturated with diethyl ether and collected by filtration to yield the title compound (8.6 g, 92% yield). 1H NMR 400 MHz (DMSO-d6): δ8.83 (m, 1H); 8.53 (m,1H); 7.65 (m, 1H); 4.23 (s, 2H); 4.07 (m, 2H); 1.16 (m, 3H).

Workup

temperatureThe reaction was heated for another 5 hours
temperaturecooled to room temperature
extractionthe reaction mixture was extracted with EtOAc (3×275 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe resulting residue was triturated with diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-39f1d524ff6c4d50b218d7c9df1a6c64
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369086B1

Reaction notes

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