Hydrazine → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid hydrazide

HRID 1183279Notes

Reaction equation

HRID 1183279 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH3:18])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)C.[NH2:20][NH2:21]>CCO.[Cl-].[Na+].O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[O:9][N:8]=[C:7]([CH3:18])[C:6]=2[CH2:5][C:4]([NH:20][NH2:21])=[O:3])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 66577263[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]acetic acid ethyl ester

Product 1

HCID 66577599[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid hydrazide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid ethyl ester (0.114 g, 0.37 mmol) in EtOH (4 mL) was added hydrazine (1M in THF; 2 mL), and the reaction was sealed and stirred at 80° C. overnight. The mixture was poured into brine and extracted with EtOAc. The combined organic layers were washed with H2O and brine, and then dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customthe reaction was sealed
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6bad6fec8af4b348d842d8d5eadd162
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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