Ethyl 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylate → 5-Methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid

HRID 1875088Notes

Reaction equation

HRID 1875088 reaction equation
[CH3:1][C:2]1[NH:6][C:5](=[O:7])[NH:4][C:3]=1[C:8]([O:10]CC)=[O:9]>[OH-].[Na+]>[CH3:1][C:2]1[NH:6][C:5](=[O:7])[NH:4][C:3]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 222231Ethyl 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylate

Product 1

HCID 135585675-Methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylate (1.00 g, 5.88 mmol) in 3N NaOH (5.88 mL) was heated to 65° C. for 2 h then cooled to RT. The mixture was filtered then added dropwise to a stirred solution of concentrated H2SO4 (1.10 mL) in water (7.35 mL). The mixture was stirred for 2 h then filtered. The solid was washed with water (2×10 mL) then dried under vacuum to give 0.65 g (78%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.21 (d, 1H), 10.52 (br. s., 1H), 9.77-10.21 (m, 1H), 1.95-2.35 (m, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. additionthen added dropwise to a stirred solution of concentrated H2SO4 (1.10 mL) in water (7.35 mL)
  3. filtrationthen filtered
  4. washThe solid was washed with water (2×10 mL)
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-c8134bb47e564ace9d85bf2004d550dd
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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