Stannous chloride dihydrate → 4-[(3-Methyl-1,2-benzisoxazol-4-yl)oxy]aniline

HRID 527515Notes

Reaction equation

HRID 527515 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.O.O.[Sn](Cl)Cl>CCO>[CH3:1][C:2]1[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 679604203-Methyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole2×

Product 1

HCID 679606614-[(3-Methyl-1,2-benzisoxazol-4-yl)oxy]anilineYield 33.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

3-methyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole (Intermediate 11, 100 mg) was dissolved under nitrogen atmosphere in 5.0 ml of EtOH. Tin(II) chloride dihydrate (417 mg, 1.85 mmol) was added. The reaction mixture was then stirred at 90° C. for 5 hours. After removal of the volatiles, water was added and the reaction mixture was extracted two times with ethyl acetate. The collected organic layers were washed with a 5% aqueous solution of NaHCO3, dried over sodium sulphate, filtered and evaporated. The crude obtained was purified by a NH column and eluted with DCM/MeOH (100/0, then a gradient from 100/0 to 90/10, then 90/10) to afford 30 mg of the title compound.

Workup

  1. customAfter removal of the volatiles, water
  2. additionwas added
  3. extractionthe reaction mixture was extracted two times with ethyl acetate
  4. washThe collected organic layers were washed with a 5% aqueous solution of NaHCO3
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude obtained
  9. customwas purified by a NH column
  10. washeluted with DCM/MeOH (100/0

Sources & evidence

ORD record
ord-cb82aca0a4224a9bb8824a84d38dc547
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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