methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate → HCID 178498600, compound

HRID 2221613Notes

Reaction equation

HRID 2221613 reaction equation
C([O:8][C:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1

Participants

4

Reactant 1

HCID 22930789methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 178498600HCID 178498600, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (15.00 g), 5% palladium on carbon (10.92 g) and tetrahydrofuran (200 mL) was stirred under a hydrogen atmosphere at room temperature for 1 hr. After removing palladium on carbon by filtration, the mother liquid was concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-hydroxy-1-phenyl-1H-pyrazole-5-carboxylate (10.30 g, yield 97%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). The crystals were recrystallized from tetrahydrofuran-isopropyl ether. melting point: 227-228° C.

Workup

  1. customAfter removing palladium on carbon
  2. filtrationby filtration
  3. concentrationthe mother liquid was concentrated

Sources & evidence

ORD record
ord-8790bbf7bccc4f668203a13e976a7ff4
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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