Sodium Hydroxide → 2-[3-(2-Methylpyrazol-3-yl)phenyl]aceticacid

HRID 1777151Notes

Reaction equation

HRID 1777151 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([O:16]CC)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[N:3]1.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90241563ethyl 2-(3-(1-methyl-1H-pyrazol-5-yl)phenyl)acetate

Product 1

HCID 902414232-[3-(2-Methylpyrazol-3-yl)phenyl]aceticacid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(3-(1-methyl-1H-pyrazol-5-yl)phenyl)acetate (300 mg, 1.2 mmol) in MeOH (6 mL) was added aqueous NaOH (1.5 mL, 40 W %). The mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated and the residue dissolved in water and adjusted pH to 5-6 with 2N of HCl. The solution was then extracted with EtOAc and the combined organic layers were concentrated to give the crude product which was used directly in the next step. LCMS (m/z): 231.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in water
  3. extractionThe solution was then extracted with EtOAc
  4. concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record
ord-babb454864ee48bb9b4c941547be46f5
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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