Acetic Acid → HCID 15407393, compound

HRID 850078Notes

Reaction equation

HRID 850078 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:9]([C:19]#[N:20])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:21]([O:23]CC)=[O:22].[OH-].[Na+].O.C(O)(=O)C>C(O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[C:9]([C:19]#[N:20])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19366045HCID 19366045, compound

Product 1

HCID 15407393HCID 15407393, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution (17 ml) of ethyl 5-amino-1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylate (1.7 g) in ethanol was added 2 N aqueous sodium hydroxide solution (3 ml) with stirring, and the mixture was refluxed under heating for 2 hours. After the completion of the reaction, the reaction mixture was poured into water and neutralized with acetic acid. The precipitated crystals were recrystallized from a mixed solvent of dioxane and water to give 0.64 g of 5-amino-1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylic acid, melting point 212° C. (decomposition).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the completion of the reaction
  4. customThe precipitated crystals were recrystallized from a mixed solvent of dioxane and water

Sources & evidence

ORD record
ord-2b9e94c44d164189afe804b2cfbebf1a
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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