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

HRID 416578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416578
[O:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4][NH:3]1.I[CH2:16][CH2:17][CH2:18][CH3:19].[H-].[Na+].Cl>CN(C=O)C>[CH2:16]([N:3]1[C:2](=[O:1])[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4]1)[CH2:17][CH2:18][CH3:19]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 222665143,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Produkt 1

HCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrileAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-010) (770 mg, 4.1 mmol) was dissolved in DMF (15 mL) and to the reaction mixture was added 1-iodobutane (0.51 mL, 4.5 mmol) and sodium hydride (60% oil suspension, 180 mg, 4.5 mmol), and the reaction mixture was stirred at room temperature for 3 h. To the reaction mixture was added dilute hydrochloric acid (1 mol/L, 60 mL) and the reaction mixture was extracted with ethyl acetate (150 mL), washed with brine (50 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (610 mg, 61%) as a white crystal.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate (150 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-21e4444d95a943bbba79fa9cef6bb9e0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088924B2

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