Hydrochloric Acid → 1-(Propan-2-yl)-1H-imidazole-4-carboxylic acid

HRID 2355289Notes

Reaction equation

HRID 2355289 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=1)=[O:7].Cl>O.CO.O1CCCC1>[CH:13]([N:11]1[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=[CH:10]1)([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 20769004Methyl 1-(propan-2-yl)-1H-imidazole-4-carboxylate

Product 1

HCID 401522241-(Propan-2-yl)-1H-imidazole-4-carboxylic acidYield 161.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of lithium hydroxide monohydrate (1.06 g, 25.1 mmol) in water (8 ml) to a solution of 1-isopropyl-1H-imidazole-4-carboxylic acid methyl ester (1.41 g, 8.38 mmol) in methanol (10 ml) and tetrahydrofuran (8 ml). Stir at room temperature for 20 hrs. Concentrate to give a solid. Dissolve the solid in a small amount of water and adjust to pH 4 with 5N hydrochloric acid. Wash the aqueous layer with ethyl acetate, and then concentrate the aqueous layer to provide the crude product as a solid (2.09 g). MS (m/z): 155 (M+H).

Workup

  1. concentrationConcentrate
  2. customto give a solid
  3. washWash the aqueous layer with ethyl acetate
  4. concentrationconcentrate the aqueous layer

Sources & evidence

ORD record
ord-eaa471a8a42d4174b29e7f402fd0875f
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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