benzyl (1H-imidazol-yl)hexanoate → (1H-imidazol-1-yl)hexanoic acid

HRID 1583418Notes

Reaction equation

HRID 1583418 reaction equation
[N:1]1([CH:6]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH:5]=[CH:4][N:3]=[CH:2]1>C(O)(C)C.[Pd]>[N:1]1([CH:6]([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]([OH:9])=[O:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 86740497benzyl (1H-imidazol-yl)hexanoate

Product 1

HCID 20260582(1H-imidazol-1-yl)hexanoic acidYield 82.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 45.1 g of benzyl (1H-imidazol-1-yl)hexanoate in 200 ml of isopropanol was hydrogenated over 10% palladium on carbon. Filtration and evaporation of the solvent gave 24.9 g (80%) of (1H-imidazol-1-yl)hexanoic acid, mp 135°-137° C.

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-45eed90e67c24929b2f1de893be3d1e9
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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