Hydrochloric Acid → HCID 178524130, compound

HRID 1093630Notes

Reaction equation

HRID 1093630 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[NH:8][N:7]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1.O>[OH:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[NH:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178468636HCID 178468636, compound

Product 1

HCID 178524130HCID 178524130, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 5-(4-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (5.8 g, 0.018 mole) in a mixture of methanol (50 mL) and THF (180 mL) was added 10% Pd/C (2 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 5 hours. The reaction mixture was then filtered through celite, and the celite was washed with methanol. The filtrate was collected and concentrated under reduced pressure afford 4.05 g (97%) of 5-(4-Benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester. LCMS: 233.08 (M+1)+, 97%. To a stirred solution of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (4 g, 0.01724 mol) in a mixture of 1,4-dioxane (88 mL) and H2O (88 mL) was added NaOH (1.57 g, 0.03793 mol) and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was then acidified with concentrated HCl solution. The mixture was concentrated and the resulting precipitate was isolated by filtration and dried to afford 3.1 g (76%) of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid. LCMS: 205.05 (M+1)+, 91.6%.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe resulting precipitate was isolated by filtration
  3. customdried

Sources & evidence

ORD record
ord-08cd0a0f27e243a081a661dfda4c391d
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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