Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate → HCID 178432586, compound

HRID 1487873Notes

Reaction equation

HRID 1487873 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]([CH3:17])=[N:14][CH:13]=1>CO.[OH-].[Na+]>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]1[N:16]=[C:15]([CH3:17])[NH:14][CH:13]=1

Participants

4

Reactant 1

HCID 90029434Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate2×

Product 1

HCID 178432586HCID 178432586, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-methyl-3-(2-methyl-1H-imidazol-5-yl)benzoate (compound 7.1, 219 mg, 0.95 mmol) was dissolved in a mixture of methanol (20 mL) and aqueous sodium hydroxide (5 mL, 2M). The resulting solution was heated at 50° C. for 16 hrs, then the reaction was cooled to room temperature and the organic solvent was removed under reduced pressure. The resulting aqueous residue was acidified to pH 3-4 with aqeuous HCl (2 M). The resulting solids were collected and dried to yield 128 mg (62%) of the title compound as a white solid. m/z (ES−) 215 (M−H)−.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customthe organic solvent was removed under reduced pressure
  3. customThe resulting solids were collected
  4. customdried

Sources & evidence

ORD record
ord-f7a01a2fb1104955a0034c4b350eb532
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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