Réaction #2186197

Équation de réaction

1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinolin-7-ol

DMF

POCl3

→

desired product

Rendement 60.0%

1 -(2-Fluoro-ethyl)7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde

Rendement 60.0%

Conditions de réaction

Traitement

1. 1
   Températurecooled to RT
2. 2
   Extractionextracted with ethyl acetate
3. 3
   LavageThe combined organic phases are washed with brine
4. 4
   Séchagedried over sodium sulphate
5. 5
   Autreevaporated
6. 6
   Autrechromatographed (silica gel, ethyl acetate/petroleum ether 1:2)

Mode opératoire

290 mg (1.48 mmol) 1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinolin-7-ol are dissolved in 5 mL DMF. 0.15 mL POCl3 are added dropwise at 0° C. The reaction mixture is slowly heated to 50° C., stirred an additional 3 h at this temperature, then cooled to RT and extracted with ethyl acetate and an aqueous saturated solution of sodium bicarbonate. The combined organic phases are washed with brine, dried over sodium sulphate and evaporated. The residue is column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2) to yield 200 mg (60%) desired product as a brown solid.

Source