1-(3,4-Dimethylphenyl)hydrazine hydrochloride → 4-[(3-bromo-2-methoxyphenyl)hydrazinylidene]-2-(3,4-dimethylphenyl)-5-methylpyrazol-3-one

HRID 59625

Reaction equation

HRID 59625 reaction equation
C(O[C:4](=[O:20])[C:5](=[N:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[C:12]=1[O:18][CH3:19])[C:6](=O)[CH3:7])C.Cl.[CH3:22][C:23]1[CH:24]=[C:25]([NH:30][NH2:31])[CH:26]=[CH:27][C:28]=1[CH3:29].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[CH3:22][C:23]1[CH:24]=[C:25]([N:30]2[C:4](=[O:20])[C:5](=[N:9][NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[C:12]=3[O:18][CH3:19])[C:6]([CH3:7])=[N:31]2)[CH:26]=[CH:27][C:28]=1[CH3:29]

Participants

6

Reactant 3

HCID 1737401-(3,4-Dimethylphenyl)hydrazine hydrochlorideHCID 517045Sodium AcetateHCID 178472845HCID 178472845, compound

Product 1

HCID 1784863784-[(3-bromo-2-methoxyphenyl)hydrazinylidene]-2-(3,4-dimethylphenyl)-5-methylpyrazol-3-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of ethyl-2-[(3-bromo-2-methoxyphenyl)hydrazono]-3-oxobutanoate (10 g) prepared as in Example 15, and 3,4-dimethylphenylhydrazine hydrochloride (6.05 g) and sodium acetate (2.63 g) in acetic acid (150 mL) was stirred and heated to about 80° C. to about 90° C. for about 3 hours. The reaction mixture was cooled to about room temperature and stirred for about 1 hour. The reaction mixture was filtered to give a solid, which was washed with acetic acid. The solid obtained was stirred in water for about 30 minutes at about room temperature, which was then filtered, washed with water and dried at about 55° C. to about 60° C. Yield: 11 g

Workup

  1. temperatureheated to about 80° C. to about 90° C. for about 3 hours
  2. temperatureThe reaction mixture was cooled to about room temperature
  3. stirringstirred for about 1 hour
  4. filtrationThe reaction mixture was filtered
  5. customto give a solid, which
  6. washwas washed with acetic acid
  7. customThe solid obtained
  8. filtrationwhich was then filtered
  9. washwashed with water
  10. customdried at about 55° C. to about 60° C

Sources & evidence

ORD record
ord-1056531128df4c94bfd4e1c666651145
Source dataset
uspto-grants-2016_09
Patent number
US09440927B2

Linked notes

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