Nitric Acid → 2,5-Dimethyl-1H-imidazole-4-carbaldehyde

HRID 1863371Notes

Reaction equation

HRID 1863371 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[C:5]([CH2:7][OH:8])[N:6]=1.[N+]([O-])(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[C:5]([CH:7]=[O:8])[N:6]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 12647302HCID 12647302, compound

Product 1

HCID 132064322,5-Dimethyl-1H-imidazole-4-carbaldehyde

Procedure

A 42.2 gm. portion of 2,5-dimethyl-4-imidazolemethanol and 44.8 ml. of concentrated nitric acid are mixed. When the initial reaction subsides, the solution is heated on a steam bath for one hour. The reaction mixture is neutralized with concentrated aqueous sodium carbonate, then concentrated under vacuum. After leaching the residue with 150 ml. of hot ethanol several times, the combined organic solutions are concentrated under vacuum. Chromatographing the residual oil on silica gel gives a solid which is recrystallized from iso-propanol-ethyl acetate to give the desired product, m.p. 164.5°-166° C.

Workup

  1. customWhen the initial reaction subsides
  2. temperaturethe solution is heated on a steam bath for one hour
  3. concentrationconcentrated under vacuum
  4. concentrationof hot ethanol several times, the combined organic solutions are concentrated under vacuum
  5. customChromatographing the residual oil on silica gel gives a solid which
  6. customis recrystallized from iso-propanol-ethyl acetate

Sources & evidence

ORD record
ord-0ccbe7e2a7104772aa0848b51b20d44e
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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