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

HRID 1075964Notes

Reaction equation

HRID 1075964 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]([OH:10])CO)=[CH:5][N:4]=[C:3]1[N+:11]([O-:13])=[O:12].CO>O>[CH3:1][N:2]1[C:6]([CH:7]=[O:10])=[CH:5][N:4]=[C:3]1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 232737231-(1-Methyl-2-nitro-1H-imidazol-5-yl)ethane-1,2-diol

Product 1

HCID 1003901-Methyl-2-nitro-1H-imidazole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.15 g. of 1-methyl-2-nitro-5-(1,2-dihydroxyethyl)imidazole in 200 ml. of methanol, a solution of 3.6 g. of NaIO4 in 85 ml. of water is added with stirring. The precipitate which forms is filtered off and washed with methanol which is then added to the filtrate. By evaporation to dryness under vacuum a residue is obtained which is extracted several times with ethyl acetate. After concentration of the collected extracts, a crystalline product is obtained, which after recrystallization from ethyl acetate melts at 114°-115° C. Yield 2.5 g. (96%).

Workup

  1. filtrationThe precipitate which forms is filtered off
  2. washwashed with methanol which
  3. additionis then added to the filtrate
  4. customBy evaporation to dryness under vacuum a residue
  5. customis obtained which
  6. extractionis extracted several times with ethyl acetate
  7. customAfter concentration of the collected extracts, a crystalline product is obtained
  8. customwhich after recrystallization from ethyl acetate melts at 114°-115° C

Sources & evidence

ORD record
ord-0c6c4ec9171b4b9d93a6c5b90677b8f0
Source dataset
uspto-grants-1976_05
Patent number
US03954789

Reaction notes

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