Sodium Hydroxide → HCID 17822716, compound

HRID 1744585Notes

Reaction equation

HRID 1744585 reaction equation
C([CH:3]([C:33]([OH:35])=[O:34])[N:4]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:21]([C:31]#[N:32])[CH:20]=1)[C:5]([C:7]1[CH:8]=[N:9][N:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:6])C.[OH-].[Na+]>C(O)C>[C:31]([C:21]1[CH:20]=[C:19]([N:4]([C:5]([C:7]2[CH:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:11]=2)=[O:6])[CH2:3][C:33]([OH:35])=[O:34])[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])#[N:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22227852HCID 22227852, compound

Product 1

HCID 17822716HCID 17822716, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(3-cyano-4-neopentyloxyphenyl)-N-[1(4-fluorophenyl)pyrazol-4-ylcarbonyl]glycine (1.5 g) was added to ethanol (15 ml). 10% aqueous sodium hydroxide solution (10 ml) was added and the mixture was stirred at a refluxing temperature for 30 min. The solvent was evaporated under reducer pressure. To the residue was added dilute hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A mixed solvent of chloroform-n-hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous acetic acid to give the title compound (0.9 g), melting point: 274–275° C./decomposition

Workup

  1. customThe solvent was evaporated under reducer pressure
  2. additionTo the residue was added dilute hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was evaporated under reduced pressure
  7. additionA mixed solvent of chloroform-n-hexane was added to the residue
  8. customcrystallization
  9. customThe crystals were recrystallized from hydrous acetic acid

Sources & evidence

ORD record
ord-f2f00aeb8b324eeebd6922cc2013f391
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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