Methanol → 4-bromo-N-ethylisoquinolin-1-amine

HRID 1922899

Reaktionsgleichung

Reaktionsgleichung von HRID 1922899
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][CH:3]=1.CO.[CH2:15]([NH2:17])[CH3:16]>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17][CH2:15][CH3:16])=[N:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 6341EthylamineHCID 4597664-Bromo-1-chloroisoquinoline

Produkt 1

HCID 596052034-bromo-N-ethylisoquinolin-1-amineAusbeute 88 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 4-bromo-1 chloroisoquinoline (0.831 g, 3.43 mmol) in MeOH (10.3 mL, 254 mmol) was added ethylamine (70% in water, 1.1 mL). The mixture was heated at 50° C. for 16 h. The mixture was concentrated. The residue was partitioned between water (20 mL) and DCM (20 mL). DCM layer was separated. The aqueous layer was extracted with DCM (10 mL) The combined DCM solutions were dried (Na2SO4). Filtration and concentration gave 4-bromo-N-ethylisoquinolin-1-amine (0.761 g, 88%). LCMS: M+H+=251.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between water (20 mL) and DCM (20 mL)
  3. customDCM layer was separated
  4. extractionThe aqueous layer was extracted with DCM (10 mL) The combined DCM solutions
  5. dry with materialwere dried (Na2SO4)
  6. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-ac312d68479d428696847172550e0583
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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