Triethylamine → 7-Methoxy-3,4-dihydroquinolin-2(1H)-one

HRID 255185

Reaktionsgleichung

Reaktionsgleichung von HRID 255185
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH2:13](N(CC)CC)C.C[Si](C=[N+]=[N-])(C)C>ClCCl.CO.C(#N)C>[CH3:13][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 167693TrimethylsilyldiazomethaneHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Produkt 1

HCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22226298HCID 22226298, VerbindungLösungsmittel

Versuchsvorschrift

A mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (3.0 g, 17 mmol) and triethyl amine (3.14 mL, 22 mmol) in dichloromethane/methanol/acetonitrile (10:1:10, 168 mL) was treated with (trimethylsilyl)diazomethane (2M solution in hexanes, 10.25 mL, 20.5 mmol). It was stirred over night at room temperature, the solvent was removed under reduced pressure and chromatography on silica gel with hexanes/acetone (1:1) gave 2.2 g (67%) of the product as a colorless solid.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure and chromatography on silica gel with hexanes/acetone (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ce70ae46bc034020b05d60f45d7f6552
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875715B2

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