Nitric Acid → 5-Methyl-2-phenyl-1H-imidazole-4-carbaldehyde

HRID 1863369Notes

Reaction equation

HRID 1863369 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][OH:14].[N+]([O-])(O)=O>O.[OH-].[Na+]>[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH:13]=[O:14]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 836581H-Imidazole-4-methanol, 5-methyl-2-phenyl-

Product 1

HCID 135486495-Methyl-2-phenyl-1H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A 102.1 gm. portion of 5-methyl-2-phenyl-4-imidazolemethanol is dissolved in 765 ml. of concentrated HNO3. The solution is cooled in an ice bath and allowed to stand for 16 hours. The solution is heated on a steam bath for 30 minutes, diluted with 2.3 liters of water and neutralized with 50% NaOH while cooling in an ice bath. The solid is collected, dried, recrystallized from 200 ml. of ethanol and then from one liter of 1:2 ethanol:water giving the desired product, m.p. 102°-115° C.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. temperatureThe solution is heated on a steam bath for 30 minutes
  3. temperaturewhile cooling in an ice bath
  4. customThe solid is collected
  5. customdried
  6. customrecrystallized from 200 ml

Sources & evidence

ORD record
ord-54d4b7b86fb247beb3a37698d18cbf63
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

Loading…