Water → (5-Nitroquinolin-2-yl)methanol

HRID 2182697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182697
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:14]=[O:15])=[N:9]2)([O-:3])=[O:2].O1CCCC1.[BH4-].[Na+].O>CO>[OH:15][CH2:14][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[N:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 47370745-Nitroquinoline-2-carbaldehyde

Produkt 1

HCID 4913360(5-Nitroquinolin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

700 mg (3.46 mmol) of 5-nitroquinoline-2-carbaldehyde are dissolved in 13 ml of methanol and 7.0 ml of tetrahydrofuran and mixed at 0° C. with 523 mg (13.9 mmol) of sodium borohydride. After 5 hours, the reaction is brought to a halt by adding water. The solvent is removed in a vacuum, the residue is taken up in dichloromethane and water, the aqueous phase is extracted with dichloromethane, and the combined organic phases are dried on sodium sulfate. After the solvent is removed, and after purification on silica gel with hexane-ethyl acetate (0-100%), 390 mg (55% of theory) of the product is obtained.

Aufarbeitung

  1. customThe solvent is removed in a vacuum
  2. extractionwater, the aqueous phase is extracted with dichloromethane
  3. customthe combined organic phases are dried on sodium sulfate
  4. customAfter the solvent is removed
  5. customafter purification on silica gel with hexane-ethyl acetate (0-100%), 390 mg (55% of theory) of the product
  6. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-9c7eca9df1444ec5815c86defd53b8e0
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897224B2

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