5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide → 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide

HRID 892578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892578
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:16]2[C:21]3[CH:22]=[C:23]([C:26]#[N:27])[CH:24]=[CH:25][C:20]=3[O:19][C:18]([CH3:29])([CH3:28])[CH2:17]2)=[N+:13]([O-:15])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:26]([C:23]1[CH:24]=[CH:25][C:20]2[O:19][C:18]([CH3:29])([CH3:28])[CH2:17][CH:16]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N+:13]=3[O-:15])[C:21]=2[CH:22]=1)#[N:27]

Komponenten

4

Edukt 1

HCID 538667995-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide

Produkt 1

HCID 540062792-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxideAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

0.21 g of 5-benzyloxy-2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide in 90 ml of methanol was hydrogenated over 10% palladium-on-carbon at room temperature and under atmospheric pressure for 30 minutes. The catalyst was removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel using dichloromethane/methanol (19:1) for the elution to give 0.05 g of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-5-hydroxypyridine N-oxide in the form of an off-white solid of melting point 224° C (from ethyl acetate).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-c1f4e5455bb042079414747f21d49b07
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118694

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