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

HRID 231633Notes

Reaction equation

HRID 231633 reaction equation
[OH-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.Cl>CN(C)C=O.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[N:16][CH:17]=1)([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2794558Diethyl 2-(5-nitropyridin-2-yl)malonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.7 g (67.5 mmol) of powdered NaOH are introduced into 10.8 g (675 mmol) of diethyl malonate in 30 ml of dimethylformamide at room temperature, with cooling, a solution of 5 g (31 mmol) of 2-chloro-5-nitropyridine in dimethylformamide is then added dropwise and the mixture is stirred at room temperature until the reaction is complete. For working up, the mixture is poured onto 500 ml of water and acidified with concentrated HCl and the precipitate is filtered off with suction and rinsed with petroleum ether.

Workup

  1. temperaturewith cooling
  2. filtrationthe precipitate is filtered off with suction
  3. washrinsed with petroleum ether

Sources & evidence

ORD record
ord-fa369518d4ad4be091cbebb3c232b350
Source dataset
uspto-grants-1989_07
Patent number
US04847382

Reaction notes

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