3-Chloro-6-(1-ethoxy-vinyl)-isoquinoline → 1-(3-Chloroisoquinolin-6-yl)ethanone

HRID 1427768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427768
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([O:14]CC)=[CH2:13])=[CH:7][CH:6]=2>O1CCOCC1.Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=2

Komponenten

4

Edukt 1

HCID 866758623-Chloro-6-(1-ethoxy-vinyl)-isoquinoline

Produkt 1

HCID 866758631-(3-Chloroisoquinolin-6-yl)ethanoneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-6-(1-ethoxy-vinyl)-isoquinoline (934 mg, 4 mmol) in 1,4-dioxane (10 mL) and hydrochloric acid (2 M, 5 mL) was stirred at room temperature for 30 minutes. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic extracts were combined, washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 9:1 to 4:1 to afford the title compound (732 mg, 89%) as a white solid. 1H NMR (300 MHz, CDCl3) δ2.77 (s, 3H), 7.88 (s, 1H), 8.05 (d, J=8.5 Hz, 1H), 8.15 (dd, J=8.5, 1.4 Hz, 1H), 8.37 (brs, H), 9.17 (s, 1H). LCMS (m/z) 206/208 [M+H], Tr=4.40 min.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-075bf4e178d444ecb3a92e335cc3efe7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933015B2

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