Hydrochloric Acid → HCID 82085459, compound

HRID 1748466Notes

Reaction equation

HRID 1748466 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:19])=[CH2:18])=[CH:13][CH:12]=2)[C:9]=1[CH3:10])=[O:4].Cl>O1CCOCC1.[C].[Pd]>[CH:17]([C:14]1[CH:13]=[CH:12][C:11]([N:8]2[C:9]([CH3:10])=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7]2)=[CH:16][CH:15]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86692434HCID 86692434, compound

Product 1

HCID 82085459HCID 82085459, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

10% palladium carbon (containing ca. 50% water; 1.00 g) was added to a solution of 1-(4-isopropenylphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid methyl ester (2.05 g) in 1,4-dioxane (40 ml) and the mixture was stirred under hydrogen atmosphere at room temperature for seven hours. The reaction solution was filtered through Celite and the filtrate was concentrated. Ethanol (40 ml), water (20 ml) and 4N aqueous solution of sodium hydroxide (20 ml) were added to the resultant residue and the mixture was stirred at 80° C. for two hours. After completion of the reaction, the reaction solution was cooled to 0° C. and 1N hydrochloric acid aqueous solution was added therein, the precipitated solid was collected by filtration to give the titled compound (1.77 g) as a white solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. additionEthanol (40 ml), water (20 ml) and 4N aqueous solution of sodium hydroxide (20 ml) were added to the resultant residue
  4. stirringthe mixture was stirred at 80° C. for two hours
  5. customAfter completion of the reaction
  6. temperaturethe reaction solution was cooled to 0° C.
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b91fd5eed02b4c99aecf756ae7992e91
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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