Sodium Hydroxide → 2-(2-Chlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid

HRID 2105764Notes

Reaction equation

HRID 2105764 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[NH:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:8]1[NH:9][C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 43445075HCID 43445075, compound

Product 1

HCID 434450792-(2-Chlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To 11.2 g of 2-(2-chloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester in 150 ml of ethanol was added 80 ml of a 2N—NaOH solution and the reaction mixture was stirred at 95° C. for 17 hours. After such time ethanol was removed in vacuo and the remaining aqueous solution was treated with a 2N HCl solution until obtaining pH=3. The precipitate was filtered and dried under high vacuum to yield 9.0 g of a pale yellow powder.

Workup

  1. customAfter such time ethanol was removed in vacuo
  2. additionthe remaining aqueous solution was treated with a 2N HCl solution
  3. customuntil obtaining pH=3
  4. filtrationThe precipitate was filtered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-8437b2061ae14434ac7abe38752c86a4
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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