Methanol → 1-Methyl-2-nitro-1H-imidazole-5-carboxaldehyde

HRID 1075966Notes

Reaction equation

HRID 1075966 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=CC2C=CC=CC=2)=[CH:5][N:4]=[C:3]1[N+:15]([O-:17])=[O:16].C[OH:19]>O=[Os](=O)(=O)=O.O>[CH3:1][N:2]1[C:6]([CH:7]=[O:19])=[CH:5][N:4]=[C:3]1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 887MethanolHCID 218198HCID 218198, compound

Product 1

HCID 1003901-Methyl-2-nitro-1H-imidazole-5-carboxaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst2×HCID 962WaterSolvent

Procedure

To a solution of 0.8 g. of 1-methyl-2-nitro-5-styrylimidazole in 300 ml. of methanol, a solution of 1.6 g. of NaIO4 in 40 ml. of water, and 0.02 g. of OsO4 are added. The mixture is stirred at room temperature for 10 hours, then an additional 0.01 g. of OsO4 is added and stirring is carried on for 8 hours. The reaction mixture is filtered and evaporated to dryness under vacuum at room temperature. The residue is extracted with ethyl acetate. After concentration of the resulting solution, 0.325 g. of the product are obtained. Yield 60%.

Workup

  1. stirringstirring
  2. customis carried on for 8 hours
  3. filtrationThe reaction mixture is filtered
  4. customevaporated to dryness under vacuum at room temperature
  5. extractionThe residue is extracted with ethyl acetate
  6. customof the product are obtained

Sources & evidence

ORD record
ord-4d3b870a92d941369d947e2916579dfa
Source dataset
uspto-grants-1976_05
Patent number
US03954789

Reaction notes

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