Hydrochloric Acid → 4-[[1-[1-(4-tert-butylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]benzoic acid

HRID 555598Notes

Reaction equation

HRID 555598 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21](=[O:32])[C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=3)[CH3:18])[C:13]([CH3:33])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21](=[O:32])[C:22]3[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=3)[CH3:18])[C:13]([CH3:33])=[N:12]2)=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178498001HCID 178498001, compound

Product 1

HCID 1784338864-[[1-[1-(4-tert-butylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 23.2 mg (0.05 mmol) of the 4-methoxycarbonylbenzoic N′-(1-(1-(4-tert-butylphenyl)-3-methyl-5-oxo-1,5-dihydropyrazol-4-ylidene)-ethyl)-hydrazide synthesized in Synthetic Example 4 in 2.0 ml of methanol, 255 μl (0.255 mmol) of 1M aqueous sodium hydroxide was added at room temperature, and the mixture was heated at from 60° C. to 80° C. for 3.5 hours. After it was cooled to room temperature, 255 μl of 1M hydrochloric acid was added, and the precipitated solid was collected by filtration to obtain 13.9 mg of the desired product as a pale brown solid (yield 61%).

Workup

  1. temperaturethe mixture was heated at from 60° C. to 80° C. for 3.5 hours
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-8bc3720fe0ab42198bd9b4670e287f24
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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