Sodium Hydroxide → HCID 68632314, compound

HRID 1798889Notes

Reaction equation

HRID 1798889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:23]=[C:22]([C:24]([O:26]C)=[O:25])[NH:21][N:20]=2)[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[NH:21][N:20]=2)[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68631479HCID 68631479, compound

Product 1

HCID 68632314HCID 68632314, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-(3,5-dichloro-4-(4-methoxybenzyloxy)phenyl)-1H-pyrazole-5-carboxylate (0.75 g, 1.85 mmol) in a mixture of THF (10 mL) and methanol (10 mL) was added 15% w/v solution of sodium hydroxide (5 mL). The mixture was stirred at room temperature for 30 minutes followed by heating at reflux for 2 h. After this time the flask was cooled to room temperature and solvent was removed in vacuo. The residue was partitioned between ethyl acetate (20 mL) and water (100 mL). The aqueous layer was acidified to pH 1 (10 M HCl, 1.5 mL) and the precipitated solids dissolved in ethyl acetate (30 mL). The organic layer was washed with an aqueous solution of sodium chloride (65 mL) and dried (MgSO4). The solution was concentrated to give 0.69 g (96%) of the Compound C as a white solid. 1H NMR δ (ppm) (DMSO-d6): 3.81 (3H, s), 5.02 (2H, s), 7.00 (2H, d, J=8.24 Hz), 7.41 (1H, s), 7.48 (2H, d, J=8.24 Hz), 8.03 (2H, s), 14.09 (1H, br s). CO2H peak not observed.

Workup

  1. additionwas added 15%
  2. temperatureby heating
  3. temperatureat reflux for 2 h
  4. temperatureAfter this time the flask was cooled to room temperature
  5. customsolvent was removed in vacuo
  6. customThe residue was partitioned between ethyl acetate (20 mL) and water (100 mL)
  7. dissolutionthe precipitated solids dissolved in ethyl acetate (30 mL)
  8. washThe organic layer was washed with an aqueous solution of sodium chloride (65 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-9c0d08b388924f88a5c71d5e176566d5
Source dataset
uspto-grants-2013_01
Patent number
US08343976B2

Reaction notes

Loading…