Water → 3-Phenyl-5-hydroxymethylquinoline

HRID 1590870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590870
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([C:17](O)=[O:18])[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Cl-].[NH4+]>O1CCCC1>[OH:18][CH2:17][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[N:9]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 109886653-Phenyl-quinoline-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 190332423-Phenyl-5-hydroxymethylquinolineAusbeute 106,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

80 g (0.32 mol) of 3-phenyl-quinoline-5-carboxylic acid are suspended in 1.6 l of abs. tetrahydrofuran under argon and 400 ml of 1 molar lithium aluminum hydride solution in tetrahydrofuran are added dropwise. In this process, the temperature may rise to 35° C. The mixture is subsequently stirred for 90 minutes and 16 ml of water and then 48 ml of saturated ammonium chloride solution are added dropwise with cooling, the mixture is subsequently stirred for 30 minutes and filtered with suction, the solid is washed with tetrahydrofuran and the filtrate is concentrated. About 80 g of crude product are obtained. The melting point of the purified compound is 110-112° C.

Aufarbeitung

  1. custommay rise to 35° C
  2. temperaturewith cooling
  3. stirringthe mixture is subsequently stirred for 30 minutes
  4. filtrationfiltered with suction
  5. washthe solid is washed with tetrahydrofuran
  6. concentrationthe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-44a3425fc72b4213822c50e800632578
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204472

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