Hydrochloric Acid → 2-bromo-4-[(2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoic acid

HRID 1881612Notes

Reaction equation

HRID 1881612 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12]([NH:14][N:15]=[C:16]([C:18]2[C:22]([OH:23])=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[N:20]([CH3:34])[N:19]=2)[CH3:17])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].CO.[OH-].[Na+].Cl>C1COCC1.O>[Br:1][C:2]1[CH:11]=[C:10]([C:12]([NH:14][N:15]=[C:16]([C:18]2[C:22]([OH:23])=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=3)[N:20]([CH3:34])[N:19]=2)[CH3:17])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86604755methyl 2-bromo-4-[(2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate

Product 1

HCID 723601032-bromo-4-[(2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoic acidYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 2-bromo-4-[(2-{1-[5-(4-tert-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]benzoate (0.455 mmol, 239.8 mg), methanol (20 mL) was added, and 1 M aqueous sodium hydroxide (2.3 mmol, 2.3 mL) was added. After 5 hours of stirring at 50° C., 14 hours of stirring at room temperature and 4 hours of stirring at 50° C., 1 M hydrochloric acid (2.3 mmol, 2.3 mL) and water were added. The precipitated solid was recovered by filtration, washed with water and dried by means of a vacuum pump to give the crude desired product as a yellow solid (203.8 mg). Further, 178 mg of the crude desired product was dissolved in THF (35 mL) and stirred at room temperature for 2 days. The insolubles were filtered off, and the filtrate was concentrated and dried by means of a vacuum pump. After addition of chloroform, the precipitated solid was recovered by filtration and dried by means of a vacuum pump to give the desired product as a pale yellow solid (150.9 mg, yield 74%).

Workup

  1. stirringof stirring at room temperature and 4 hours
  2. stirringof stirring at 50° C.
  3. filtrationThe precipitated solid was recovered by filtration
  4. washwashed with water
  5. customdried by means of a vacuum pump
  6. customto give the crude desired product as a yellow solid (203.8 mg)
  7. stirringstirred at room temperature for 2 days
  8. filtrationThe insolubles were filtered off
  9. concentrationthe filtrate was concentrated
  10. customdried by means of a vacuum pump
  11. additionAfter addition of chloroform
  12. filtrationthe precipitated solid was recovered by filtration
  13. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-a4a7d439a37746cab259224647171ad1
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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