Hydrazine → HCID 57947817, compound

HRID 340889Notes

Reaction equation

HRID 340889 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15]CC)=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][NH2:19]>CCO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([NH:18][NH2:19])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22831984HCID 22831984, compound

Product 1

HCID 57947817HCID 57947817, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-(3-fluorophenyl)isoxazole-3-carboxylate (25.8 g, 110 mmol, 1.0 equiv.) in EtOH (300 mL), was added hydrazine (10.5 mL, 330 mmol, 3.0 equiv.). The mixture was stirred at 80° C. for 1 h and then cooled to RT The precipitate was filtered, washed with H2O, and dried in vacuum to give 5-(3-fluorophenyl)isoxazole-3-carbohydrazide (20 g). The filtrate was concentrated and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give desired product (2.5 g). LRMS (M+H+) m/z 222.0.

Workup

  1. temperaturecooled to RT The precipitate
  2. filtrationwas filtered
  3. washwashed with H2O
  4. customdried in vacuum

Sources & evidence

ORD record
ord-f1ae6985176a42469bc56f4b6e813db3
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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