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

HRID 2419651Notes

Reaction equation

HRID 2419651 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 2-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 2-propanol-ethyl acetate

Sources & evidence

ORD record
ord-5b940e22f28a4bd08d27dcd81b06e1c0
Source dataset
uspto-grants-1978_08
Patent number
US04107308

Reaction notes

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