Hydrochloric Acid → 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylic acid

HRID 2046018Notes

Reaction equation

HRID 2046018 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]1[CH2:15][CH:14]1[C:16]([O:18]CC)=[O:17].O.[OH-].[Li+].CO.Cl>O1CCCC1.O.C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]1[CH2:15][CH:14]1[C:16]([OH:18])=[O:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 71143804ethyl 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate

Product 1

HCID 711437792-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate (746 mg, 2.76 mmol) in tetrahydrofuran (15 mL) was added lithium hydroxide monohydrate (232 mg, 5.52 mmol) in water (5.00 mL) at rt. Added methanol (5.00 mL) and stirred for 15 h at rt. Removed solvent. Obtained a white solid. Redissolved in water (15 mL) and neutralized with 5.5 mL of 1.0 M HCl. Removed solvent and azetroped with toluene (2×10 mL). Dried for 20 h and obtained 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylic acid as a white powder. MS (ESI) 243 (M+H); Rf=1.35 (Condition A).

Workup

  1. customObtained a white solid
  2. customDried for 20 h

Sources & evidence

ORD record
ord-55e5aef1f14f46f08ceab5f1260fcad5
Source dataset
uspto-grants-2013_11
Patent number
US08592423B2

Reaction notes

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