Dichloromethane → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1750084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750084
CS(O/[N:6]=[C:7]1\[CH2:8][CH2:9][C:10]2[C:15]\1=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)(=O)=O.B(F)(F)F.CS(Cl)(=O)=[O:24].C(Cl)Cl>ClCCCl.Cl[Ti](Cl)(Cl)Cl>[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][NH:6][C:7]2=[O:24])=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 6356Boron trifluorideHCID 31297Methanesulfonyl chlorideHCID 89350921HCID 89350921, Verbindung

Produkt 1

HCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To the solution of intermediate 17 (7.76 g, 30.4 mmol) in 1,2-dichloroethane (150 mL) was added BF3 (5.52 mL, 48.7 mmol, in MeOH), MsCl (3.8 mL, 48.7 mmol) and TiCl4 (5.35 mL, 48.7 mmol). The mixture was stirred at rt for 5 h. CH2Cl2 (150 mL) was then added to the reaction mixture. The solution was washed with water and brine. The water layer was neutralized by aqueous Na2CO3 to pH=7 and was extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1) to give 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (intermediate 18) (5.1 g, 95%) as a white solid.

Aufarbeitung

  1. washThe solution was washed with water and brine
  2. extractionwas extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b23d3f47896a40f28a4cc2ff5039ba4a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156822B2

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