Stannous chloride dihydrate → 5-amino-2-benzylisoquinolin-1(2H)-one

HRID 749209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749209
O.O.[Sn](Cl)Cl.[CH2:6]([N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[N+:23]([O-])=O)[C:14]1=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:23][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[CH:22][N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:14]2=[O:26]

Komponenten

6

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 184445282-benzyl-5-nitroisoquinolin-1(2H)-one

Produkt 1

HCID 184445335-amino-2-benzylisoquinolin-1(2H)-oneAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Tin(II) chloride dihydrate (1.21 g, 5.36 mmol) was added to a stirred solution of 2-benzyl-5-nitroisoquinolin-1(2H)-one (300 mg, 1.07 mmol) in anhydrous ethanol (20 mL). The reaction mixture was stirred at reflux for 20 h. The resulting mixture was cooled to room temperature, treated with saturated aqueous sodium bicarbonate to pH=11 and diluted with water (100 mL). The obtained mixture was extracted with ethyl acetate (3×70 mL). The combined organic fractions were dried over anhydrous Na2SO4, filtered and evaporated to give 5-amino-2-benzylisoquinolin-1(2H)-one (248 mg, 1.0 mmol, 93% yield) as an orange foam.

Aufarbeitung

  1. temperatureat reflux for 20 h
  2. extractionThe obtained mixture was extracted with ethyl acetate (3×70 mL)
  3. dry with materialThe combined organic fractions were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d50aa7129329405187ee1311c434aeaa
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402596B2

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