Hydrazine hydrate (1:1) → HCID 86631568, compound

HRID 551332Notes

Reaction equation

HRID 551332 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Br:23])[C:20]([F:24])=[C:19]([Br:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:26][N:27]1C(=O)C2=CC=CC=C2C1=O.O.NN>C(O)C>[NH2:27][CH2:26][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Br:23])[C:20]([F:24])=[C:19]([Br:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86631566HCID 86631566, compound

Product 1

HCID 86631568HCID 86631568, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[[2-chloro-4-[5-(3,5-dibromo-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl]methyl]phthalimide (0.75 g) in ethanol (10 mL) was added hydrazine monohydrate (1.07 g). The mixture was heated to reflux for 1 hour and then cooled to room temperature. The resulting mixture was filtered and concentrated under reduced pressure. The residue was dissolved in chloroform (10 mL) and filtered, and the filtrate was washed with water (10 mL) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by column chromatography on silica gel eluted with methanol-ethyl:acetate (1:9) to afford the title compound as a pale yellow resin (0.51 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform (10 mL)
  6. filtrationfiltered
  7. washthe filtrate was washed with water (10 mL) and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto provide a residue
  11. customThe residue was purified by column chromatography on silica gel
  12. washeluted with methanol-ethyl:acetate (1:9)

Sources & evidence

ORD record
ord-5ebf9bfbf9444a9ca8ac685016b49c75
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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