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

HRID 650229Notes

Reaction equation

HRID 650229 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][N:12]=[C:13]([C:20](=[O:22])[CH3:21])[CH2:14][C:15](OCC)=[O:16])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([N:11]2[C:15](=[O:16])[CH2:14][C:13]([C:20](=[O:22])[CH3:21])=[N:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 867532112-chloro-4-[N'-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid

Product 1

HCID 217146532-Chloro-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1.9 gm. (5.8 mmoles) of 2-chloro-4-[N′-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid in 20 ml of ethanol was added at room temperature 6 ml. of aqueous 1 M sodium carbonate. The mixture was left at roomtemperature temperature overnight. The resulting mixture was acidifed to pH 3 with 6 M hydrochloric acid and the resulting solid collected by filtration and dried. The 2-chloro-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid had a melting point of >250° C.

Workup

  1. additionTo a suspension of 1.9 gm
  2. filtrationthe resulting solid collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-acdecb0f4ed24e3d8ea00d6e0ad40b4d
Source dataset
uspto-grants-2001_08
Patent number
US06271373B1

Reaction notes

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