Dimethylformamide → Diethyl (3-nitropyridin-2-yl)propanedioate

HRID 1601141Notes

Reaction equation

HRID 1601141 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+].CN(C)C=O.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1>O.C(O)(=O)C>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 13147345Diethyl (3-nitropyridin-2-yl)propanedioate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

50 g (0.31 mol) of diethyl malonate were added, a little at a time, at not more than 50° C. to a mixture of 7.5 g (0.31 mol) of sodium hydride and 50 ml of dimethylformamide, with ice-cooling. After the mixture had cooled to room temperature (approximately 25° C.), it was treated with g (0.173 mol) of 2-chloro-3-nitropyridine. After approximately 15 hours, the reaction mixture was diluted with water, acidified using acetic acid and extracted using ethyl acetate. The organic phases were combined, washed and dried, and the solvent was removed under reduced pressure. The excess malonic ester was distilled off at elevated temperature and reduced pressure ("high vacuum"). This gave 43 g (66%) of the title compound as a yellow oil (purity approximately 75%).

Workup

  1. temperaturewith ice-cooling
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. distillationThe excess malonic ester was distilled off at elevated temperature and reduced pressure ("high vacuum")

Sources & evidence

ORD record
ord-4857b5f1e46445c2aa7e20ef98033d55
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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