HCID 66988335, compound → 3-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochloride

HRID 530696Notes

Reaction equation

HRID 530696 reaction equation
[ClH:1].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11]>[Pd].O1CCCC1.O>[ClH:1].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 66988335HCID 66988335, compound

Product 1

HCID 669882033-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochlorideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

60 mg of 10% palladium-on-charcoal are introduced into a solution of 387 mg (2.1 mmol) of (E)-3-(5-methyl-1H-imidazol-4-yl)acrylic acid hydrochloride in 8 ml of 1/1 tetrahydrofuran/water, purged beforehand with nitrogen. The reaction medium is placed under a hydrogen atmosphere and then stirred for 19 hours. After filtering through Celite and rinsing thoroughly with dichloromethane, the recovered filtrate is concentrated under vacuum. The crude residue is taken up in toluene and concentrated again in order to remove the residual water, and is then taken up in a mixture of heptane and diisopropyl ether (80/20) with stirring for about 2 hours. The desired product precipitates and is filtered off under vacuum. 326 mg (83%) of 3-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochloride are obtained in the form of a white solid.

Workup

  1. custompurged
  2. filtrationAfter filtering through Celite
  3. washrinsing thoroughly with dichloromethane
  4. concentrationthe recovered filtrate is concentrated under vacuum
  5. concentrationconcentrated again in order
  6. customto remove the residual water
  7. additionis then taken up in a mixture of heptane and diisopropyl ether (80/20)
  8. stirringwith stirring for about 2 hours
  9. customThe desired product precipitates
  10. filtrationis filtered off under vacuum

Sources & evidence

ORD record
ord-65df8d2f79404a06a63254122210c8c7
Source dataset
uspto-grants-2016_05
Patent number
US09353083B2

Reaction notes

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