Sodium Hydroxide → 3-(1-Methyl-1H-pyrazol-5-yl)benzoic acid

HRID 2201991Notes

Reaction equation

HRID 2201991 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=[N:3]1.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69687203methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoate

Product 1

HCID 185488473-(1-Methyl-1H-pyrazol-5-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(1-methyl-1H-pyrazol-5-yl)benzoate (200 mg, 0.93 mmol) in MeOH (3 mL) was added aqueous NaOH (1 mL, 0.4M). The mixture was stirred at room temperature for 2 h. The reaction solution was concentrated and the residue was dissolved in water and adjusted pH to 5-6 with 2N of HCl. The solution was extracted with EtOAc (2×20 mL). The combined organic layers were dried and concentrated to give the target crude product which was used directly in the next step. LCMS (m/z): 203.1 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionThe solution was extracted with EtOAc (2×20 mL)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customto give the target crude product which

Sources & evidence

ORD record
ord-5392cbf77c414074af9b79ceba508738
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

Loading…