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

HRID 2419701Notes

Reaction equation

HRID 2419701 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 1 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 isopropanol-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 1 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 isopropanol-ethyl acetate

Sources & evidence

ORD record
ord-e9ed05eca66b4462936ddebf2c549241
Source dataset
uspto-grants-1978_08
Patent number
US04107307

Reaction notes

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