Acetic Acid → HCID 59355663, compound

HRID 1627006Notes

Reaction equation

HRID 1627006 reaction equation
C(O)(=O)C.O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:29]([F:32])([F:31])[F:30])[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]([Cl:28])=[C:23]([N+:25]([O-])=O)[CH:24]=3)[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1>[Fe].C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:29]([F:30])([F:32])[F:31])[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]([Cl:28])=[C:23]([CH:24]=3)[NH2:25])[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 59355668HCID 59355668, compound

Product 1

HCID 59355663HCID 59355663, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

An iron powder (3.46 g) was added to a mixture of acetic acid (0.38 g), water (15 ml) and ethanol (30 mL) at room temperature, and thereto was added 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-chloronitrobenzene (2.73 g) obtained by Reference Production Example 19 at 75° C. After stirring at 75° C. for 50 minutes, the reaction mixture was filtrated and then the filtrate was 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-chloroaniline (1.65 g).

Workup

  1. customobtained by Reference Production Example 19 at 75° C
  2. filtrationthe reaction mixture was filtrated
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcf73f4c38bd468086ab7ba973eee8c4
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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