Sodium Hydroxide → 5-Methyl-2-phenyl-1H-imidazole-4-carbaldehyde

HRID 1704189Notes

Reaction equation

HRID 1704189 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].[OH-].[Na+]>[N+]([O-])(O)=O.O>[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 14798Sodium HydroxideHCID 836581H-Imidazole-4-methanol, 5-methyl-2-phenyl-

Product 1

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

Reagents, catalysts & solvents 2

HCID 944Nitric AcidSolventHCID 962WaterSolvent

Procedure

5-Methyl-2-phenyl-4-imidazolemethanol (102.1 g) is dissolved in concentrated nitric acid (765 ml). 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 water (2.3 liters) and neutralized with 50% sodium hydroxide while cooling in an ice bath. The solid is collected, dried, recrystallized from ethanol (200 ml) and then from 1:2 ethanol:water (1000 ml) giving the title 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 ethanol (200 ml)

Sources & evidence

ORD record
ord-fec77bd6d1f441ef9387b82c794cc234
Source dataset
uspto-grants-1978_11
Patent number
US04126444

Reaction notes

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