3,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole → {4-[(3,6-Dimethyl-1,2-benzisoxazol-4-yl)oxy]phenyl}amine

HRID 527521Notes

Reaction equation

HRID 527521 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 679598393,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole2×HCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 67960640{4-[(3,6-Dimethyl-1,2-benzisoxazol-4-yl)oxy]phenyl}amineYield 139.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole (Intermediate 20, 208 mg) was dissolved in ethanol (10.0 ml) and tin chloride dihydrate (991 mg, 4.39 mmol) was added. The reaction mixture was stirred and heated at reflux for 4 hours. After the removal of the volatiles, water was added and the reaction mixture was extracted two times with ethyl acetate. The collected organic were dried over sodium sulphate, filtered and evaporated to afford 260 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customAfter the removal of the volatiles, water
  4. additionwas added
  5. extractionthe reaction mixture was extracted two times with ethyl acetate
  6. dry with materialThe collected organic were dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e39700682b174194a77c8d26339e2c7f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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