Methanol → 1-(4-Amino-2-methylquinolin-3-yl)ethanol

HRID 414050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414050
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13](=[O:15])[CH3:14].[BH4-].[Na+].CO.ClCCl.CO>C(O)(C)C.O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]=1[CH:13]([CH3:14])[OH:15]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 6722971-(4-Amino-2-methylquinolin-3-yl)ethanoneHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanol

Produkt 1

HCID 52439581-(4-Amino-2-methylquinolin-3-yl)ethanolAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

1-(4-amino-2-methyl-3-quinolinyl)-ethanone (2 g) was added all at once as a solid to a stirred suspension of sodium borohydride (1.13 g) in isopropanol (50 ml). The mixture was refluxed for several hours until the reaction was complete based on thin-layer chromatography (silica gel, 10% methanol/dichloromethane). Methanol (10 ml) and water (5 ml) were added and the mixture was allowed to cool slowly to room temperature. Most of the solvent was evaporated under vacuum, and the concentrate partitioned between water and ethyl acetate. The ethyl acetate extract was dried (saturated sodium chloride wash, sodium sulfate) and the ethyl acetate removed under vacuum. The resulting solid was recrystallized from acetonitrile to give 1.5 g of crystals, mp 214°.

Aufarbeitung

  1. temperatureThe mixture was refluxed for several hours until the reaction
  2. customMost of the solvent was evaporated under vacuum
  3. customthe concentrate partitioned between water and ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customwas dried
  6. wash(saturated sodium chloride wash, sodium sulfate)
  7. customthe ethyl acetate removed under vacuum
  8. customThe resulting solid was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-0f0345ee7cc042c2b5817f6618712fcc
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04789678

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