Water → 2-Benzyl-5-nitropyridine

HRID 1059382Notes

Reaction equation

HRID 1059382 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=2)(C(OCC)=O)C(OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(O)C>[CH2:7]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 18670110Diethyl 2-phenyl-2-(5-nitropyridin-2-yl)malonate

Product 1

HCID 186702212-Benzyl-5-nitropyridineYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 g of diethyl 2-phenyl-2-(5-nitropyridin-2-yl)malonate was dissolved in 50 ml of ethanol. After adding 10 ml of water and 10 ml of conc. sulfuric acid, the mixture was heated under reflux for 8 hours. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted 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 632 mg of the title compound as reddish brown crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customAfter the completion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n- hexane)

Sources & evidence

ORD record
ord-af31bdbee61549fda7913392f362f055
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

Loading…