Hydrazine hydrate (1:1) → HCID 67041295, compound

HRID 606116Notes

Reaction equation

HRID 606116 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][NH2:15])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67041242HCID 67041242, compound

Product 1

HCID 67041295HCID 67041295, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-{2-[3-(4-fluorophenyl)isoxazol-5-yl]ethyl}-1H-isoindole-1,3(2H)-dione (27.14 g, 80.70 mmol), hydrazine hydrate (9.8 mL, 202 mmol), and ethanol (700 mL) was heated at reflux under nitrogen for two hours. The reaction mixture was filtered to remove a solid, and the filtrate was concentrated under reduced pressure. The resulting oil was dissolved in ethyl acetate, and the solution was washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 16.14 g of 2-[3-(4-fluorophenyl)isoxazol-5-yl]ethylamine as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for two hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove a solid
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe resulting oil was dissolved in ethyl acetate
  7. washthe solution was washed sequentially with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f53c3a0369343e6811cc50430182d39
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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