Ethanol → 4-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide

HRID 387851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387851
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([S:13][C:14]3[S:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:22]([NH2:24])=[O:23].[Cl-].[NH4+].C(O)C.O>[Fe].CO.C(OCC)(=O)C.CN(C)C=O>[NH2:19][C:16]1[S:15][C:14]([S:13][C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:22]([NH2:24])=[O:23])[CH:5]=3)[N:10]=[CH:9][CH:8]=2)=[CH:18][CH:17]=1

Komponenten

9

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 229366247-Methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamide

Produkt 1

HCID 229362694-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamideAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

After suspending 7-methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamide (320 mg, 0.885 mmol), iron (247 mg, 4.43 mmol) and ammonium chloride (481 mg, 8.85 mmol) in an ethanol (8 ml)-water (2 ml)-dimethylformamide (1 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 15 minutes. After completion of the reaction, the reaction mixture was filtered with celite and washed in a tetrahydrofuran-methanol mixed solvent. After adding ethyl acetate to the organic layer, it 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:methanol=20:1), and the fraction containing the target substance was concentrated to obtain the title compound (164 mg, 0.495 mmol, 56%) 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 a tetrahydrofuran-methanol mixed solvent
  6. additionAfter adding ethyl acetate to the organic layer, it
  7. washwas washed with water and saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationthe drying agent was filtered off
  10. distillationthe filtrate was distilled off under reduced pressure
  11. customThe obtained crude product
  12. additionthe fraction containing the target substance
  13. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-22a3654e9582409d90347fed788c1c57
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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