Hydrochloric Acid → 2-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 489300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489300
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([C:8](=[O:18])[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].Cl>C1COCC1>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH:8]([OH:18])[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Produkt 1

HCID 222665102-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrileAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (10 mg, 0.04 mmol) was dissolved in THF (1 mL), and to the reaction mixture was added sodium borohydride (2.1 mg, 0.056 mmol), and the reaction mixture was stirred at room temperature for 10 min. To the reaction mixture was added diluted hydrochloric acid (1 mol/L, 3 mL), and the reaction mixture was extracted with ethyl acetate (10 mL), washed with brine (5 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crystalloid residue was recrystallized from methylene chloride to give 2-butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-013) (7.4 mg, 75%) as a white crystal.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
  2. washwashed with brine (5 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe obtained crystalloid residue was recrystallized from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-ea657da50f8340c4aa23af9d67fcec5e
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977266B2

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