Sodium Hydroxide → 2-(3-Isopropyl-ureido)-isonicotinic acid

HRID 1665161Notes

Reaction equation

HRID 1665161 reaction equation
C([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH:6]=1)C.[OH-].[Na+]>CO>[CH:15]([NH:14][C:12](=[O:13])[NH:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][N:8]=1)[C:4]([OH:18])=[O:3])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67086709HCID 67086709, compound

Product 1

HCID 643934662-(3-Isopropyl-ureido)-isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-Isopropyl-ureido)-isonicotinic acid ethyl ester (130 mg, 0.52 mmol) in MeOH (5 ml) is added 2 M NaOH (2.5 ml) and the resulting solution is stirred for 1.5 hours at room temperature. The solvent is removed in vacuo and sat. aq. NH4Cl solution is added. The pH of the aqueous phase is adjusted to 1 using 1 M HCl and the product extracted into EtOAc, dried (MgSO4) the solvent removed in vacuo to afford 2-(3-Isopropyl-ureido)-isonicotinic acid as a white solid; [M+H]+ 224

Workup

  1. customThe solvent is removed in vacuo and sat. aq. NH4Cl solution
  2. additionis added
  3. extractionthe product extracted into EtOAc
  4. dry with materialdried (MgSO4) the solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-f0ed600f4cc440869e4fcbcda167b858
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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