4-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline → 4-(2-Fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline

HRID 393589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393589
C([O:8][C:9]1[C:10]([CH3:39])=[CH:11][C:12]([F:38])=[C:13]([CH:37]=1)[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)C1C=CC=CC=1>[Pd].CN(C=O)C.CO>[F:38][C:12]1[CH:11]=[C:10]([CH3:39])[C:9]([OH:8])=[CH:37][C:13]=1[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 1

HCID 226466314-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline

Produkt 1

HCID 226465164-(2-Fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinolineAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (274 mg, 0.5 mmol) and 10% palladium-on-charcoal catalyst (274 mg) in DMF (10 ml) and methanol (10 ml) was stirred under hydrogen at 5 atmospheres pressure for 3 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation. The resulting solid was suspended in ether, collected by filtration and washed with methylene chloride and isopropanol to give 4-(2-fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (134 mg, 25 60%).

Aufarbeitung

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation
  3. filtrationcollected by filtration
  4. washwashed with methylene chloride and isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-a5e7f3b374bf48429129d6a2d2043894
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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