Sodium Hydroxide → 8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577480
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.C1C(=O)N([I:21])C(=O)C1.[OH-].[Na+]>OS(O)(=O)=O>[I:21][C:12]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:13])[NH:9][CH2:8][CH2:7]2

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 120273N-IodosuccinimideHCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

Produkt 1

HCID 867237068-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a mixture of 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (53a, 1.7 g, 9.6 mmol) in conc. H2SO4 (40 mL) was added portionwise NIS (2.4 g, 11 mmol) at 0° C. The mixture was stirred at room temperature for 14 hours. The mixture was chilled to 0° C. and basified with aq. NaOH to pH 8. The mixture was extracted with EtOAc (5×60 mL). The combined organic layers were washed with brine (3×60 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 1:1) to give 8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (53b, 2.1 g, 79%) as a yellow solid.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (5×60 mL)
  2. washThe combined organic layers were washed with brine (3×60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e33e935d22ed42268b3a03efff591a36
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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