Sodium Hydroxide → HCID 178433263, compound

HRID 540387Notes

Reaction equation

HRID 540387 reaction equation
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][C:3]=1[CH:7]=[CH:8][C:9]([Cl:11])=[O:10].[OH-].[Na+].[H][H]>[Pd]>[CH3:1][C:2]1[N:6]=[CH:5][NH:4][C:3]=1[CH2:7][CH2:8][C:9]([Cl:11])=[O:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compoundHCID 178433262HCID 178433262, compound

Product 1

HCID 178433263HCID 178433263, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
80 °C

Procedure

50 mg of palladium-on-charcoal at 10% are added to 500 mg (2.65 mmol) of 3-(5-methyl-3H-imidazol-4-yl)acrylic acid chloride in 10 ml of a 0.5N solution of sodium hydroxide. The reaction mixture is placed under 6 bar of hydrogen pressure and stirred at 80° C. for 72 hours. After having filtered off the catalyst through celite, the residue is acidified to pH 2 with hydrochloric acid, concentrated to dryness and taken up in ethanol. The insoluble material is filtered off and the filtrate is concentrated to dryness. 102 mg of 3-(5-methyl-3H-imidazol-4-yl)propanoic acid chloride are obtained in the form of a white powder with a yield of 16%.

Workup

  1. filtrationAfter having filtered off the catalyst through celite
  2. concentrationconcentrated to dryness
  3. filtrationThe insoluble material is filtered off
  4. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-22909198763949ee8182ca80a00743fa
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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