Hydrochloric Acid → HCID 72359925, compound

HRID 2103849Notes

Reaction equation

HRID 2103849 reaction equation
[OH:1][C:2]1[C:3]([C:17](=[N:19][NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)=[O:22])[CH3:18])=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH3:15])=[CH:9][CH:8]=1.CO.[OH-].[Na+].Cl>O>[OH:1][C:2]1[C:3]([C:17](=[N:19][NH:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)=[O:22])[CH3:18])=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH3:15])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604745HCID 86604745, compound

Product 1

HCID 72359925HCID 72359925, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[4-hydroxy-1-methyl-5-(4-n-propylphenyl)-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.166 mmol, 72.2 mg), methanol was added, and 1 M aqueous sodium hydroxide (5 eq., 0.831 mL) was added at room temperature. After 10 minutes of stirring at room temperature and 2 hours of stirring at 60° C., the reactor was cooled to room temperature, and 1 M hydrochloric acid (5 eq., 0.831 mL) and water were added. The precipitated solid was recovered by filtration, washed with water and dried by means of a vacuum pump, and the residue was further purified by silica gel thin layer chromatography (chloroform/methanol=10/1). After addition of chloroform/n-hexane, the precipitated solid was recovered by filtration and dried to give the desired product as a yellow solid (47.1 mg, yield 67%).

Workup

  1. stirringof stirring at 60° C.
  2. temperaturethe reactor was cooled to room temperature
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump
  6. customthe residue was further purified by silica gel thin layer chromatography (chloroform/methanol=10/1)
  7. additionAfter addition of chloroform/n-hexane
  8. filtrationthe precipitated solid was recovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-0708ea60cf5049a8b1240cf28dfbb391
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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