Hydrochloric Acid → 3-(4-t-Butylphenyl)-1-(4-cyanophenyl)-4-hydroxycarbonyl-2-methyl-2H-pyrazol-5-one

HRID 1740076Notes

Reaction equation

HRID 1740076 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:30])[N:13]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)[C:14](=[O:21])[C:15]=2[C:16]([O:18]CC)=[O:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(O)C.Cl>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]([CH3:30])[N:13]([C:22]3[CH:23]=[CH:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=3)[C:14](=[O:21])[C:15]=2[C:16]([OH:18])=[O:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11430Potassium CarbonateHCID 218376543-(4-t-Butylphenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-one

Product 1

HCID 218376453-(4-t-Butylphenyl)-1-(4-cyanophenyl)-4-hydroxycarbonyl-2-methyl-2H-pyrazol-5-oneYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 34.5 g of 3-(4-t-butylphenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-one, 23.6 g of potassium carbonate, 621 ml of ethanol and 69 ml of water was refluxed under heating for 9 hours. The reaction solution was cooled to room temperature and adjusted to pH 1-2 with dilute hydrochloric acid. The resulting crystals were collected by filtration and dried under reduced pressure. The resulting crude crystals were recrystallized in methanol-ethyl acetate to give 12.2 g of the title compound as colorless crystals. The mother liquor was concentrated, and the resulting residue was crystallized in chloroform-diethyl ether to give 8.3 g of the title compound as pale yellow crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 9 hours
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried under reduced pressure
  5. customThe resulting crude crystals were recrystallized in methanol-ethyl acetate

Sources & evidence

ORD record
ord-48618f7e41264a1d939488fba7a219f5
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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