Hydrochloric Acid → 3-Methyl-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

HRID 567694

Reaction equation

HRID 567694 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][N:12]=[C:13]([C:20](=[O:22])[CH3:21])[CH2:14][C:15](OCC)=[O:16])[C:5]([OH:7])=[O:6].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:15](=[O:16])[CH2:14][C:13]([C:20](=[O:22])[CH3:21])=[N:12]1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 86751496Ethyl 3-(4-carboxy-2-methylphenylhydrazono)-4-oxopentanoate

Product 1

HCID 154850873-Methyl-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of a 5 g. (34 mmoles) of 3-methyl-4-[N′-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid in 25 ml. of ethanol and 25 ml. of water was added with stirring 34.3 ml. of a 1 M sodium carbonate solution. The mixture was stirred at room temperature for 24 hours. The resulting mixture was acidified to pH 3 with 6 M hydrochloric acid and the resulting solid was collected by filtration, washed with water and dried. The 3-methyl-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid has a melting point of >250° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a93c14bc62bf422facdd01b28f2fe87f
Source dataset
uspto-grants-2001_01
Patent number
US06180628B2

Linked notes

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