Sodium Hydroxide → 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid

HRID 1019040Notes

Reaction equation

HRID 1019040 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6]/[CH:7]=[CH:8]/[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:10]=1.[OH-].[Na+]>CO.O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6]/[CH:7]=[CH:8]/[C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18399528methyl 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

Product 1

HCID 183995244-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acidYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate (1.37 g; 4 mmol) in methanol (20 ml) was treated at reflux for 4 hours with a solution of sodium hydroxide (0.32 g; 8 mmol) in water (24 ml). After evaporation to dryness the residue was acidified at pH 6 with 12N HCl. The resulting solid was triturated with water and subsequently with ether to give 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoic acid. Yield: 46%

Workup

  1. customAfter evaporation to dryness the residue
  2. customThe resulting solid was triturated with water and subsequently with ether

Sources & evidence

ORD record
ord-d3d21bf655c047a59f9b20dc381e5bf7
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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