8-Nitro-7-quinolinecarboxaldehyde → (3-Fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol

HRID 513658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513658
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[N+:10]([C:13]1[C:14]([CH:23]=[O:24])=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)([O-:12])=[O:11]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:23]([C:14]2[C:13]([N+:10]([O-:12])=[O:11])=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[OH:24])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 117695548-Nitro-7-quinolinecarboxaldehyde2×HCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 68183441(3-Fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanolAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-Fluorophenyl magnesium bromide (1 M solution in THF; 0.86 ml, 4.33 mmol) was added dropwise to a solution of 8-nitroquinoline-7-carbaldehyde (Intermediate 204) (0.35 g, 1.73 mmol) in dry THF (5 ml) at −78° C. and the mixture was stirred at −78° C. for 1 h. The reaction was quenched with saturated NH4Cl solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (0.3 g, 58%).

Aufarbeitung

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-fe13ca0ea02f414ab50d65eaf24e1a38
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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