Hydrochloric Acid → HCID 72360000, compound

HRID 1881593Notes

Reaction equation

HRID 1881593 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH2:16][CH3:17])[N:14]=[C:13]([C:18](=[N:20][NH:21][C:22]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)=[O:23])[CH3:19])[C:12]=2[OH:34])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH2:16][CH3:17])[N:14]=[C:13]([C:18](=[N:20][NH:21][C:22]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[O:23])[CH3:19])[C:12]=2[OH:34])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604749HCID 86604749, compound

Product 1

HCID 72360000HCID 72360000, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 4-[(2-{1-[5-(4-t-butylphenyl)-1-ethyl-4-hydroxy-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.032 mmol, 15.0 mg), methanol (1.5 mL) was added, and 1 M aqueous sodium hydroxide (0.162 mmol, 0.162 mL) was added at room temperature. After 30 minutes of stirring at room temperature and 1.25 hours of stirring at 60° C., the reactor was cooled to 0° C., and 1 M hydrochloric acid (0.162 mmol, 0.162 mL) and water were added. The precipitated solid was recovered by filtration, washed with water, dried by means of a vacuum pump and purified by silica gel thin layer chromatography (chloroform/methanol=10/1) to give the desired product as a yellow solid (6.4 mg, yield 44%).

Workup

  1. stirringof stirring at 60° C.
  2. temperaturethe reactor was cooled to 0° C.
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump
  6. custompurified by silica gel thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-28a909cfcd384bc48267f8251554b020
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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