Stannous Chloride → HCID 21100343, compound

HRID 2053385Notes

Reaction equation

HRID 2053385 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)[CH:13]=1>C(OCC)(=O)C.O>[NH2:23][C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[C:12]([C:6]3[C:5]([Cl:4])=[CH:10][CH:9]=[CH:8][C:7]=3[Cl:11])[O:16][N:15]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 21100346HCID 21100346, compound

Product 1

HCID 21100343HCID 21100343, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tin (II) chloride (135 mg, 0.6 mmol) was added to a solution of 5-(2,6-dichlorophenyl)-3-(3-nitrophenyl)isoxazole compound (100 mg, 0.3 mmnol) in ethyl acetate (20 mL). The resulting solution was heated at reflux for 3 h and then cooled to room temperature. The reaction mixture was diluted with water (20 mL). The mixture was extracted with ethyl acetate twice. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was concentrated under reduced pressure to give the title compound as an off-white solid, 71 mg.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 3 h
  3. extractionThe mixture was extracted with ethyl acetate twice
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. concentrationThe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8203d31cb854725b2fb58a12188764e
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

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