Hydrochloric Acid → 2-Amino-7-(4-methylpyridin-2-yl)quinoline dihydrochloride

HRID 1060009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060009
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][C:14]#[N:15])=[C:10]([N+:18]([O-])=O)[CH:9]=2)[CH:3]=1.C(=O)([O-])O.[Na+].[ClH:26]>C(O)(=O)C.CN(C)C=O.C(OCC)(=O)C.O1CCOCC1.[Fe]>[ClH:26].[ClH:26].[NH2:15][C:14]1[CH:13]=[CH:12][C:11]2[C:10](=[CH:9][C:8]([C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=3)=[CH:17][CH:16]=2)[N:18]=1

Komponenten

9

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 545662564-(4-Methylpyridin-2-yl)-2-nitrocinnamonitrile

Produkt 1

HCID 186674862-Amino-7-(4-methylpyridin-2-yl)quinoline dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 4-(4-methylpyridin-2-yl)-2-nitrocinnamonitrile (1.32 g) in acetic acid (5 ml) and N,N-dimethylformamide (5 ml) was added iron powder (1.63 g), and the mixture was stirred at 100° C. for 3 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 5-10% methanol in dichloromethane). The compound obtained was dissolved in ethyl acetate, and a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) was added. The precipitate was collected by filtration and dried to give 2-amino-7-(4-methylpyridin-2-yl)quinoline dihydrochloride (482 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 50 g, 5-10% methanol in dichloromethane)
  7. customThe compound obtained
  8. filtrationThe precipitate was collected by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f187048786764ac99758c75380598765
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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