Acetic Acid → HCID 178449926, compound

HRID 636729Notes

Reaction equation

HRID 636729 reaction equation
[CH3:1][C:2]([N+:5]([O-:7])=O)([CH3:4])[CH3:3].C(O)(=O)C.[NH:12]1[CH:16]=[C:15]([CH:17]=O)[CH:14]=[N:13]1>C(O)C.[Zn]>[NH:12]1[CH:16]=[C:15]([CH:17]=[N+:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[O-:7])[CH:14]=[N:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 178449926HCID 178449926, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 1,1-dimethylnitroethane (546.0 mg, 5.29 mmol) and zinc (515.5 mg, 7.89 mmol) in ethanol (3.0 ml) was added acetic acid (950.0 mg, 15.8 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 45 minutes. After cooling the mixture to 5° C. again, pyrazole-4-carbaldehyde (255.4 mg, 2.66 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 (chloroform/methanol=10/1).

Workup

  1. stirringThe mixture was stirred at room temperature for 45 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 (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-3dda7806b29f49648e56e330b8acec06
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

Loading…