Ethanol → HCID 58533551, compound

HRID 1627001Notes

Reaction equation

HRID 1627001 reaction equation
[CH3:1][N:2]([N:26]=O)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:4]=1.C(O)C.O>[Zn].C(O)(=O)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH2:13][C:12]([C:18]3[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=3)([C:14]([F:17])([F:15])[F:16])[O:11][N:10]=2)[CH:4]=1)[NH2:26]

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 86661621HCID 86661621, compound

Product 1

HCID 58533551HCID 58533551, compoundYield 113.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of N-methyl-N-nitroso-3-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]aniline (1.00 g) obtained by Reference Production Example 9, ethanol (2 ml), water (2 ml) and acetic acid (2 ml) was added zinc (695 mg) at room temperature. After stirring at room temperature for 5 hours, this mixture was filtrated. To the filtrate was added anhydrous sodium hydrogen carbonate, and then the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain crude N-methyl-N-{3-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl}hydrazine (1.1 g).

Workup

  1. filtrationthis mixture was filtrated
  2. additionTo the filtrate was added anhydrous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6aa9628121da4b79a4d3e9fbff9a1c7e
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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