Hydrazine hydrate (1:1) → HCID 67356224, compound

HRID 405705Notes

Reaction equation

HRID 405705 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:34]([F:37])([F:36])[F:35])[O:13][N:12]([CH3:14])[C:11]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][N:20]4C(=O)C5C(=CC=CC=5)C4=O)=[C:17]([CH3:33])[CH:16]=3)=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.NN>C(O)C.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:34]([F:36])([F:35])[F:37])[O:13][N:12]([CH3:14])[C:11]([C:15]3[CH:32]=[CH:31][C:18]([CH2:19][NH2:20])=[C:17]([CH3:33])[CH:16]=3)=[CH:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 533715112-{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzyl}-isoindole-1,3-dione

Product 1

HCID 67356224HCID 67356224, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

837 mg of 2-{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzyl}-isoindole-1,3-dione (Example I14) and 500 mg hydrazine hydrate in 25 ml ethanol were heated at reflux for 2 hours under stirring. The mixture was cooled and diluted with diethyl ether. The solid was filtered off and the filtrate was evaporated. The residue was dissolved in 100 ml of ether and washed with water. The organic phase was dried and evaporated. The residue was purified on silica gel (eluent dichloromethane/methanol 4:1) affording 4-[5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzylamine as a resin in 65% yield. 1H-NMR (CDCl3, δ in ppm): 7.44 (s, 2H), 7.37 (m, 2H), 7.28 (m, 2H), 5.33 (s, 1H), 3.88 (s, 2H), 2.99 (s, 3H), 2.34 (s, 3H).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe solid was filtered off
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in 100 ml of ether
  6. washwashed with water
  7. customThe organic phase was dried
  8. customevaporated
  9. customThe residue was purified on silica gel (eluent dichloromethane/methanol 4:1)

Sources & evidence

ORD record
ord-a9eaee1ed88c4f3f825471820d9b03d6
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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