Pyridine → 6-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehyde

HRID 579469

Reaktionsgleichung

Reaktionsgleichung von HRID 579469
BrC1C(=O)[O:4][C:5]2[C:10](C=1C)=[CH:9]C=[C:7]([OH:13])[CH:6]=2.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:21](C(C(F)(F)F)=O)C(C(F)(F)F)=O>C(Cl)Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:20]2[NH:15][C:16](=[O:21])[CH:17]=[CH:18][C:19]=2[C:6]=1[CH:7]=[O:13]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 53375453-Bromo-7-hydroxy-4-methylchromen-2-one

Produkt 1

HCID 866834296-Hydroxy-2-oxo-1,2-dihydroquinoline-5-carbaldehydeAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Compound 1 (38 g, 249.6 mmol) and pyridine (21.7 g, 275.0 mmol) were dissolved in DCM (750 mL). (CF3CO)2O (57.7 g, 275.0 mmol) was added dropwise at 0° C. After that the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with DCM (500 mL), washed with 1N HCl, concentrated. The residue was purified by silica gel column (PE:EA=10:1), afforded compound 2 (45 g, 72%) as white solid.

Aufarbeitung

  1. washwashed with 1N HCl
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column (PE:EA=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e66b7c0178974a83b40a588fcf4809cb
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040714B2

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