Acetic Acid → HCID 153418, compound

HRID 636726Notes

Reaction equation

HRID 636726 reaction equation
[CH3:1][C:2]([N+:5]([O-:7])=O)([CH3:4])[CH3:3].C(O)(=O)C.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=O>C(O)C.[Zn]>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[N+:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[O-:7]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 153418HCID 153418, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 1,1-dimethylnitroethane (545.5 mg, 5.29 mmol) and zinc (516.6 mg, 7.90 mmol) in ethanol (3.0 ml) was added acetic acid (950.1 mg, 15.8 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 20 minutes. After cooling the mixture to 5° C. again, 2-pyridinecarbaldehyde (283.9 mg, 2.65 mmol) was added dropwise to the mixture while stirring and stirred at room temperature overnight. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (ethyl acetate).

Workup

  1. stirringThe mixture was stirred at room temperature for 20 minutes
  2. stirringwhile stirring
  3. stirringstirred at room temperature overnight
  4. filtrationZinc acetate in the mixture was filtered off
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-57d4cdddfbc34a89b741a82f29758ef1
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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