Reaction #2186197

Reaction equation

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

DMF

POCl3

→

desired product

Yield 60.0%

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

Yield 60.0%

Conditions

Workup

1. 1
   Temperaturecooled to RT
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe combined organic phases are washed with brine
4. 4
   Dryingdried over sodium sulphate
5. 5
   Otherevaporated
6. 6
   Otherchromatographed (silica gel, ethyl acetate/petroleum ether 1:2)

Procedure

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