Reaktion #54058

Reaktionsgleichung

MeI

NaH

N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide

NaH

→

title compound

N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]-N-methylbenzamide

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA round bottom flask equipped with a stir bar and under argon atmosphere
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe combined organics were subsequently washed with brine
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigechromatographed
7. 7
   Waschento elute product
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A round bottom flask equipped with a stir bar and under argon atmosphere was charged with NaH (60% in oil) (0.04 mmol, 1 equiv) and 1 mL of THF. Another vessel containing N-[6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolin-4-ylmethyl]benzamide (Example 3) was diluted with THF and this solution was added to the NaH solution. Lastly, MeI (0.06 mmol, 1.5 equiv) was added and the reaction was stirred 5 hours under argon. The reaction was quenched with water and extracted with EtOAc. The combined organics were subsequently washed with brine and concentrated in vacuo. The residue was taken up in methylene chloride and adsorbed onto silica gel and flash chromatographed using 25% EtOAc/hexanes to elute product. The product fractions were pooled and concentrated in vacuo to afford 7.2 mg of the title compound as a oil.

Quelle