Aluminium lithium hydride → 2-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-one

HRID 1063563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1063563
[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[N:15]=[C:14]([C:24](OCC)=[O:25])[C:13]([F:29])=[CH:12][C:11]=2[C:10](=[O:30])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[C:11]([C:10](=[O:30])[CH:9]=1)=[CH:12][C:13]([F:29])=[C:14]([CH2:24][OH:25])[N:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 21948195Ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate

Produkt 1

HCID 219481342-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-oneAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. suspension of ethyl 7-anilino-3-fluoro-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylate (100.0 mg, 0.25 mmol) in THF (2.5 mL) was added LAH (0.750 mmol, 1M in THF) dropwise over 10 min. After 5 min. the reaction was slowly quenched with EtOAc (10 mL), was left to stir for 15 min and was concentrated in vacuo. The residue was taken up in CH2Cl2 (10 mL) and 1N HCl (5 mL) and was left to stir for 30 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. Trituation with Et2O provided 2-anilino-6-fluoro-7-(hydroxymethyl)-1-phenyl-1,8-naphthyridin-4(1H)-one (55.2 mg, 61%) as a tan solid: LCMS RT: 2.01 min, MH+: 362.3.

Aufarbeitung

  1. customAfter 5 min. the reaction was slowly quenched with EtOAc (10 mL)
  2. waitwas left
  3. concentrationwas concentrated in vacuo
  4. wait1N HCl (5 mL) and was left
  5. stirringto stir for 30 min
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1447221f41648189366dda3a622ff37
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06964971B2

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