3-Hydrazino-4-methylbenzoic acid hydrochloride → HCID 57559704, compound

HRID 1723952Notes

Reaction equation

HRID 1723952 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])[NH2:3].[C:14]([CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])O)#[N:15].[Na]>FC(F)(F)C(O)=O>[CH2:22]([O:21][C:19]([C:17]1[CH:16]=[C:14]([NH2:15])[N:2]([C:4]2[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=[CH:11][C:12]=2[CH3:13])[N:3]=1)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 567775083-Hydrazino-4-methylbenzoic acid hydrochlorideHCID 86615157Sodium 2-cyano-1-ethoxycarbonyl-ethenol

Product 1

HCID 57559704HCID 57559704, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of the above phenyl hydrazine intermediate, (50 mg, 0.247 mmol) in trifluoroacetic acid (TFA) (500 μL) was added sodium 2-cyano-1-ethoxycarbonyl-ethenol (49 mg, 0.298 mmol). The red mixture was heated to reflux for 2 h then cooled and concentrated. Purification by silica-gel chromatography (2% NH4OH/25% MeOH in EtOAc) provided 5-amino-1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (60 mg, 83%) as a white solid: ESI MS m/z 290 [C14H15N3O4+H]+.

Workup

  1. temperatureThe red mixture was heated
  2. temperatureto reflux for 2 h
  3. temperaturethen cooled
  4. concentrationconcentrated
  5. customPurification by silica-gel chromatography (2% NH4OH/25% MeOH in EtOAc)

Sources & evidence

ORD record
ord-f85574876d534432b9e95796b2e909c7
Source dataset
uspto-grants-2009_02
Patent number
US07485657B2

Reaction notes

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