Methanol → 1H-Imidazole-5-propanoic acid

HRID 6765Notes

Reaction equation

HRID 6765 reaction equation
[CH:1]1[N:5]=[CH:4][NH:3][C:2]=1/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9].CO>Cl.[Pd]>[NH:3]1[C:2]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:1][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 887MethanolHCID 736715trans-Urocanic acid2×

Product 1

HCID 706301H-Imidazole-5-propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Urocanic acid (compound i, where R2 is H)(1.38 g, 10.0 mmol) was dissolved in 5% aqueous HCl (20 ml) plus MeOH (15 ml) containing 10% Pd on carbon (100 mg) and the mixture was shaken overnight under about 30 psi H2. The catalyst was removed by filtration through a 3 cm pad of diatomaceous earth and the filtrate was concentrated to a solid and dried overnight under vacuum. The crude material was used without further purification. Mass spec. 141.4 MH+

Workup

  1. customThe catalyst was removed by filtration through a 3 cm pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated to a solid
  3. customdried overnight under vacuum
  4. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-366c487f99fe4d4cb442dff8b04764dd
Source dataset
uspto-grants-2006_08
Patent number
US07084135B1

Reaction notes

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