Ethanol → 5-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamine

HRID 387842

Reaktionsgleichung

Reaktionsgleichung von HRID 387842
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([N+:21]([O-])=O)=[CH:19][CH:20]=1.[Cl-].[NH4+].C(O)C.O>[Fe].CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([NH2:21])=[CH:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 229368146,7-Dimethoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline

Produkt 1

HCID 229363515-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiophen-2-ylamineAusbeute 138,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

After suspending 6,7-dimethoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline (1.39 g, 4.00 mmol), iron (1.12 g, 20.0 mmol) and ammonium chloride (2.18 g, 40.0 mmol) in an ethanol (32 ml)-water (8 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 5 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated to obtain the title compound (1.93 g, 5.54 mmol, 55%) as yellowish-brown crystals.

Aufarbeitung

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in ethyl acetate
  6. washThe organic layer was washed with water and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. additionthe fraction containing the target substance
  12. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5eaa8cf82938478ebcd27986a80fd4d2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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