Diethyl Malonate → Diethyl 2-(5-nitropyridin-2-yl)malonate

HRID 2281878Notes

Reaction equation

HRID 2281878 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1>O1CCCC1>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[N:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl malonate (151 g, 0.944 mol) was added dropwise under stirring to 60% sodium hydride in mineral oil (37.8 g, 0.944 mol) in dry tetrahydrofuran (1 L). After hydrogen evolution ceased, 2-chloro-5-nitropyridine (125 g, 0.787 mol) was added. The reaction mixture was refluxed for 2 hours and then the tetrahydrofuran was evaporated in vacuo to give crude diethyl (5-nitropyridin-2-yl)malonate, which was used at the next stage without purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customthe tetrahydrofuran was evaporated in vacuo

Sources & evidence

ORD record
ord-6d1db07e8cbb4d01bb9073cf038ca72b
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

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