Hydrazine hydrate (1:1) → HCID 86761694, compound

HRID 1880241Notes

Reaction equation

HRID 1880241 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C:13]2([C:37]([F:40])([F:39])[F:38])[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]([N:26]4C(=O)C5=CC=CC=C5C4=O)[CH3:25])=[CH:20][CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.NN>C(O)C>[NH2:26][CH:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH2:14][C:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:42])([F:41])[F:1])[CH:4]=3)([C:37]([F:38])([F:39])[F:40])[O:17][N:16]=2)=[CH:23][CH:22]=1)[CH3:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86761693HCID 86761693, compound

Product 1

HCID 86761694HCID 86761694, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2.80 g of N-[1-[4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]ethyl]phthalimide in 10 mL of ethanol, 0.22 g of hydrazine monohydrate was added and the resultant reaction mixture was stirred at 80° C. for 2 hours. After the completion of the reaction, the mixture was cooled down to 0° C. and the deposited insoluble substance was filtered off, followed by cleaning the filtered substance with a small amount of chloroform. The filtrate and the resultant chloroform-cleaning liquid were combined and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 30 mL of ethyl acetate and the resultant solution was washed with water (10 mL×1). Subsequently, the washed solution was dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 1.80 g of the objective substance as a yellow resinoid. This was used in the next process as it was without being further purified.

Workup

  1. customthe resultant reaction mixture
  2. customAfter the completion of the reaction
  3. temperaturethe mixture was cooled down to 0° C.
  4. filtrationthe deposited insoluble substance was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe resultant residue was dissolved in 30 mL of ethyl acetate
  7. washthe resultant solution was washed with water (10 mL×1)
  8. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto obtain 1.80 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-35f8ad52877f4b31948033594d54aee8
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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