Lithium hydroxide, monohydrate → 5-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylic acid

HRID 1260052Notes

Reaction equation

HRID 1260052 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([CH3:18])=[N:9][C:8]=1[C:19]([O:21]C)=[O:20].O.[OH-].[Li+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]([CH3:18])=[N:9][C:8]=1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58355289methyl 5-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylate

Product 1

HCID 583555335-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylic acidYield 29.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylate (3.85 g) was dissolved in methanol (26 ml)-water (24 ml), lithium hydroxide monohydrate (800 mg) was added and the mixture was heated under reflux for 2 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was adjusted to pH=7 with 1M hydrochloric acid, subjected to DIAION HP-20 (manufactured by Mitsubishi Chemical), washed with water and a fraction eluted with acetone was concentrated under reduced pressure to give the object product (1.08 g).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hr
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. washwashed with water
  6. washa fraction eluted with acetone
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-29bc1cd6b9434a009ad3e3cfe663652f
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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