Acetic Acid → HCID 59355618, compound

HRID 1627003Notes

Reaction equation

HRID 1627003 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:28]([F:31])([F:30])[F:29])[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:27])=[C:22]([N+:24]([O-])=O)[CH:23]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1>C(O)C.[Fe]>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:28]([F:30])([F:29])[F:31])[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:27])=[C:22]([CH:23]=3)[NH2:24])[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59355619HCID 59355619, compound

Product 1

HCID 59355618HCID 59355618, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

To an aqueous 2.5% acetic acid solution (19 ml) was added an iron powder (10-20 mesh; 1.89 g), followed by a suspension of 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylnitrobenzene (4.62 g) obtained by Reference Production Example 12 in ethanol (29 ml) at 75° C., and then the mixture was stirred at the same temperature for 15 minutes. To the mixture was further added an iron powder (1.80 g) at the same temperature, and the mixture was stirred at the same temperature for 1 hour. After cooling to room temperature, the reaction mixture was filtrated and washed with ethyl acetate. Then, the filtrate was extracted with an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate. 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 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylaniline (3.18 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. filtrationthe reaction mixture was filtrated
  3. washwashed with ethyl acetate
  4. extractionThen, the filtrate was extracted with an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fa2824b503d481aa95f69519283f412
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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