Stannous chloride dihydrate → HCID 67497584, Verbindung

HRID 1628225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628225
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[N+:21]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:11][C:10]=1[NH2:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 67497417HCID 67497417, Verbindung

Produkt 1

HCID 67497584HCID 67497584, VerbindungAusbeute 115,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-(benzyloxy)-3-nitrophenyl)pyridine 13.0 (1.52 g, 4.97 mmol) in ethyl acetate (20 mL) was added tin(II) chloride dihydrate (4.49 g, 19.87 mmol). The mixture was heated to reflux for 2 hours, then quenched with 100 ml 1N NaOH. The resulting mixture was stirred overnight at room temperature, then partitioned between AcOEt and water. The organic phase was dried on MgSO4 and concentrated to afford 2-(benzyloxy)-5-bromobenzenamine 13.D (1.59 g, 115% yield) which was used in the next step without any further purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customquenched with 100 ml 1N NaOH
  4. custompartitioned between AcOEt and water
  5. customThe organic phase was dried on MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19eb16209e774f2fbb40ab4d885efff4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785468B2

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