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

HRID 527515
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 527515
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

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

Produkt 1

HCID 679606614-[(3-Methyl-1,2-benzisoxazol-4-yl)oxy]anilineAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cb82aca0a4224a9bb8824a84d38dc547
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346790B2

Notizen zur Reaktion

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