Reaktion #218730

Reaktionsgleichung

4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-8-ethylquinoline-3-carboxylic acid ethyl ester

lithium tri-t-butoxyaluminohydride THF

→

title compound

Ausbeute 84.0%

4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-8-ethyl-3-(hydroxymethyl)-6-quinolinecarbonitrile

Ausbeute 84.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was refluxed overnight
2. 2
   SonstigeThe reaction was quenched with 1 mL of MeOH
3. 3
   Sonstigepartitioned between 75 mL 1M NaOH and 100 mL CH2Cl2
4. 4
   WaschenThe organic phase was washed with 1M NaOH (2×30 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeRemoval of the solvent under reduced pressure

Vorschrift

To a suspension of 100 mg (0.236 mmol) of 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-6-cyano-8-ethylquinoline-3-carboxylic acid ethyl ester in 2.8 mL anhydrous THF under nitrogen, was added 1.2 mL (5.0 eq) of 1M lithium tri-t-butoxyaluminohydride/THF. The resulting mixture was refluxed overnight with stirring. The reaction was quenched with 1 mL of MeOH and partitioned between 75 mL 1M NaOH and 100 mL CH2Cl2. The organic phase was washed with 1M NaOH (2×30 mL) and dried over MgSO4. Removal of the solvent under reduced pressure gave 75 mg (84% yield) of the title compound as a light yellow solid. The analytical sample was obtained by trituration in ether: mp: 188-189° C. LC: 3.15′; MH+: 382.

Quelle