Lithium hydroxide, monohydrate → 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid

HRID 75486Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[C:9]2[CH2:18][CH2:19][CH3:20])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of ethyl 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylate (compound 5, 1.28 g, 4.37 mmol) in THF/water (20/20 mL) was added lithium hydroxide monohydrate at room temperature. The reaction mixture was stirred at 55° C. for 12 hrs. The mixture was washed with CH2Cl2, the aqueous layer was acidified with 1N-HCl solution (pH≈6), extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product was washed with hexane to provide the title compound (740 mg, 64%) as a pale brown solid.

Workup

washThe mixture was washed with CH2Cl2
extractionextracted with CH2Cl2
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
washThe obtained product was washed with hexane

Sources & evidence

ORD record: ord-ded33343f8484d0885807ce27b121196
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835436B2

Reaction notes

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