Sodium borohydride → (6-Ethoxy-2-(ethylamino)quinolin-3-yl)methanol

HRID 1620210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620210
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH2:15][CH3:16])[C:8]([CH:17]=[O:18])=[CH:7]2)[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH2:15][CH3:16])[C:8]([CH2:17][OH:18])=[CH:7]2)[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866698196-Ethoxy-2-(ethylamino)quinoline-3-carbaldehyde2×

Produkt 1

HCID 68182224(6-Ethoxy-2-(ethylamino)quinolin-3-yl)methanolAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-ethoxy-2-(ethylamino)quinoline-3-carbaldehyde SLA 41034 (0.605 g, 2.48 mmol) in THF (50 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.094 g, 2.48 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (40 mL). After stirring for 15 min at that temperature, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give (6-ethoxy-2-(ethylamino)quinolin-3-yl)methanol SLA 41040 as an orange solid (481 mg, 79% yield).

Aufarbeitung

  1. temperaturethen cooled in an ice bath
  2. custombefore quenching by addition of a 1 N aq. HCl solution (40 mL)
  3. stirringAfter stirring for 15 min at that temperature
  4. customTHF was then removed at 40° C. under vacuum
  5. extractionthe solution was extracted with CH2Cl2 (200 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e1171a1f4ca44c57a5433b8fff729372
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772316B2

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