HCID 22997467, compound → 3-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochloride

HRID 540435Notes

Reaction equation

HRID 540435 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].CCCCCCC.C(OC(C)C)(C)C>[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

5

Reactant 2

HCID 22997467HCID 22997467, compoundHCID 66988335HCID 66988335, compound

Product 1

HCID 669882033-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochlorideYield 155.5%

Reagents, catalysts & solvents 2

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

Procedure

60 mg of palladium-on-charcoal at 10% are added to a solution of 387 mg (1.1 mmol) of (E)-3-(5-methyl-1H-imidazol-4-yl)acrylic acid hydrochloride in a 1/1 tetrahydrofuran/water mixture. The reaction medium is placed under a hydrogen atmosphere and stirred for 19 h, and then filtered through celite. The filtrate is concentrated under vacuum. The residue obtained is taken up in a heptane/diisopropyl ether mixture with stirring for 2 h. The white precipitate formed is filtered off and then dried. 326 mg of 3-(5-methyl-1H-imidazol-4-yl)propanoic acid hydrochloride are obtained in the form of a white solid with a yield of 83%.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated under vacuum
  3. customThe residue obtained
  4. stirringwith stirring for 2 h
  5. customThe white precipitate formed
  6. filtrationis filtered off
  7. customdried

Sources & evidence

ORD record
ord-61ac989c36b148929a6a478abcb60eba
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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