2-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one → 2,3,6,7,8,9-Hexahydro-2-hydroxymethyl-5-methylfuro[2,3-f]quinoline-7-one

HRID 1900717

Reaktionsgleichung

Reaktionsgleichung von HRID 1900717
[OH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[H][H]>[Pd].C(O)(=O)C>[OH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH2:9][CH2:8]3

Komponenten

5

Edukt 2

HCID 233696792-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 233697232,3,6,7,8,9-Hexahydro-2-hydroxymethyl-5-methylfuro[2,3-f]quinoline-7-oneAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (538 mg) was added to acetic acid (AcOH) (11 ml). To the obtained mixture, 10% palladium-on-carbon (323 mg) was added, and the solution was hydrogenated in the atmosphere of hydrogen at 50° C. under atmospheric pressure. After completion of the reaction, the catalyst was filtered off. The solvent was evaporated, and the residue was dissolved in chloroform. The solution was washed with aqueous sodium bicarbonate solution and water in this order, and dried. Subsequently, the solvent was evaporated to obtain 478 mg of a crude. The obtained crude was purified by silica gel column chromatography (eluent:=chloroform:methanol=100:1), to obtain 395 mg of the target compound (72.8%). This substance was recrystallized from a solvent mixture of chloroform-n-hexane. As a result, colorless powdery crystals having a melting point of 172°-173° C. were obtained.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with aqueous sodium bicarbonate solution and water in this order
  6. customdried
  7. customSubsequently, the solvent was evaporated
  8. customto obtain 478 mg of a crude
  9. customThe obtained crude
  10. customwas purified by silica gel column chromatography (eluent:=chloroform:methanol=100:1)

Quellen und Nachweise

ORD-Eintrag
ord-0f3eefda9de44bdca1059d0faf19ae01
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576324

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