Potassium Hydroxide → HCID 19881314, compound

HRID 847367Notes

Reaction equation

HRID 847367 reaction equation
C([O:3][C:4](=O)[CH:5]([C:7]1[CH:8]=[N:9][NH:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:13]=1)[CH3:6])C.Cl.[NH2:26][OH:27].[OH-].[K+]>CO>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([C:11]2[NH:10][N:9]=[CH:8][C:7]=2[CH:5]([CH3:6])[C:4]([NH:26][OH:27])=[O:3])=[CH:13][CH:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 67916073HCID 67916073, compound

Product 1

HCID 19881314HCID 19881314, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-5 °C

Procedure

10 g 5-(4-n-hexylphenyl)-1H-pyrazol-4-yl-propionic acid ethyl ester dissolved in 40 ml methanol are added rapidly to a solution of 4.2 g hydroxylamine hydrochloride and 5 g KOH in 40 ml methanol, pre-cooled to -5° C. After reaching room temperature, the reaction mixture is stirred for 24 hrs. The mixture is filtered and the solvent concentrated under vacuum. The residue is dissolved in ethyl acetate, washed with water, dried with Na2SO4 and solvent removed by evaporation under vacuum. The title compound is crystallised from ethyl ether/hexane: m.p.=150°-155° C.

Workup

  1. customAfter reaching room temperature
  2. filtrationThe mixture is filtered
  3. concentrationthe solvent concentrated under vacuum
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried with Na2SO4 and solvent
  7. customremoved by evaporation under vacuum
  8. customThe title compound is crystallised from ethyl ether/hexane

Sources & evidence

ORD record
ord-a0d98bf562d3412093629bd5155a2316
Source dataset
uspto-grants-1992_08
Patent number
US05141951

Reaction notes

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