Hydrochloric Acid → HCID 86604746, compound

HRID 1881584Notes

Reaction equation

HRID 1881584 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19](=[N:21][NH:22][C:23]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=3)=[O:24])[CH3:20])[C:14]=2[OH:35])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CO.[OH-].[Na+].Cl>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19](=[N:21][NH:22][C:23]([C:25]3[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)=[O:24])[CH3:20])[C:14]=2[OH:35])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604747HCID 86604747, compound

Product 1

HCID 86604746HCID 86604746, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[5-(4-n-hexylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.158 mmol, 75.2 mg), methanol was added, and 1 M aqueous sodium hydroxide (5 eq., 0.789 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., 0.789 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 dried to give the desired product as a yellow solid (29.4 mg, yield 40%).

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. customthe precipitated solid was dried

Sources & evidence

ORD record
ord-d8dc6020d44a4085b87ed311302d32da
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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