Hydrazine → HCID 44628234, compound

HRID 386728Notes

Reaction equation

HRID 386728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:32]([F:35])([F:34])[F:33])[O:13][N:12]=[C:11]([C:14]3[CH:31]=[CH:30][C:17]([CH2:18][N:19]4C(=O)C5C(=CC=CC=5)C4=O)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.NN>CO.C(OC)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:32]([F:34])([F:33])[F:35])[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH2:18][NH2:19])=[CH:30][CH:31]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 25183527HCID 25183527, compound

Product 1

HCID 44628234HCID 44628234, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 2-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]benzyl}-1H-isoindole-1,3(2H)-dione (0.65 g) and aqueous hydrazine solution (0.07 g) in methanol (5 mL) was refluxed for one hour. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatography to yield 1-{4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]phenyl}methanamine (0.2 g).

Workup

  1. washthe solution was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-0db47dfb6816483db59d3ac2594fd9f4
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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