Acetic Acid → Niraxostat

HRID 850071Notes

Reaction equation

HRID 850071 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:15]2[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[CH:17]=[N:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].[OH-].[Na+].O.C(O)(=O)C>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:15]2[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[N:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19366044HCID 19366044, compound

Product 1

HCID 449035NiraxostatYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution (20 ml) of ethyl 1-(3-cyano-4-neopentyloxyphenyl)pyrazole4-carboxylate (2 g) in ethanol was added 2 N aqueous sodium hydroxide solution (3.7 ml) with stirring, and the mixture was heated at 80° C. for 30 minutes. 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 solution of ethyl alcohol and water to give 0.7 g of 1-(3-cyano-4-neopentyloxyphenyl) pyrazole-4-carboxylic acid, melting point 199-200° C.

Workup

  1. customAfter the completion of the reaction
  2. customThe precipitated crystals were recrystallized from a mixed solution of ethyl alcohol and water

Sources & evidence

ORD record
ord-93cb202be4284160b65e90aa7dbb5fb1
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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