Pyridine → HCID 59018177, Verbindung

HRID 31159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31159
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:25](O)=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2.N1C=CC=CC=1>ClCCl>[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 232736625-Methoxyquinolin-8-ol

Produkt 1

HCID 59018177HCID 59018177, VerbindungAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulphonic anhydride (12 ml, 77.0 mmol) was added slowly, over approximately 5 minutes, to a stirred solution of 5-methoxy-quinolin-8-ol (Syn. Comm. 1997, 27(20), 3573-3579) (1.5 g, 8.6 mmol) and pyridine (5.5 ml, 68.5 mmol) in dichloromethane (34 ml) at 0° C., under nitrogen. The resulting mixture was allowed to warm to room temperature and stirred for a further 16 hours. The mixture was then partitioned between dichloromethane (100 ml) and saturated aqueous ammonium chloride solution (100 ml). The organic extract was further washed with water (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide a crude yellow solid. Purification by flash chromatography on silica gel, eluting with 5% ethyl acetate, 95% pentane, provided the title compound as a pale yellow solid (2.62 g, 99%). 1H-NMR (400 MHz, CDCl3): δ=4.02 (s, 3 H) 6.79 (d, 1 H) 7.50 (m, 2 H) 8.58 (dd, 1 H) 9.03 (dd, 1 H); LRMS: APCl+: m/z 308 [MH+].

Aufarbeitung

  1. customThe mixture was then partitioned between dichloromethane (100 ml) and saturated aqueous ammonium chloride solution (100 ml)
  2. extractionThe organic extract
  3. washwas further washed with water (100 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a crude yellow solid
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 5% ethyl acetate, 95% pentane

Quellen und Nachweise

ORD-Eintrag
ord-f770070bd5484eb38e028e69e41fef46
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425569B2

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