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

HRID 2281620Notes

Reaction equation

HRID 2281620 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-8c1c5e3426e34d21a5cb4469b2086406
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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