ethyl 4-(4,5-dihydro-1H-imidazol-2-yl)benzoate → ethyl 4-(1H-imidazol-2-yl)benzoate

HRID 747699Notes

Reaction equation

HRID 747699 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd]>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 22709787ethyl 4-(4,5-dihydro-1H-imidazol-2-yl)benzoate

Product 1

HCID 17788902ethyl 4-(1H-imidazol-2-yl)benzoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg (2.3 mmol) of ethyl 4-(2-imidazoline-2-yl)benzoate and 500 mg of 10% palladium/carbon were heated in 20 ml of toluene under reflux in argon atmosphere for 9 hours. The reaction liquid was diluted with ethyl acetate and filtered through Celite. The filtrate was concentrated to obtain the title compound.

Workup

  1. temperatureunder reflux in argon atmosphere for 9 hours
  2. customThe reaction liquid
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3aae55ec152741afa79a5cde7036aec0
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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