Reacción #928559

Ecuación de reacción

6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

formic acid

→

title compound

Rendimiento 90.0%

6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-1-carbaldehyde

Rendimiento 90.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 3 h
2. 2
   workup.ADDITIONpoured into ice-cold saturated aqueous sodium bicarbonate solution
3. 3
   Extracciónextracted with diethyl ether (×2)
4. 4
   SecadoThe combined organic phase was dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated in vacuo to a residue which

Procedimiento

A solution of 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, available in accordance with U.S. Pat. No. 5,089,509, the specification of which is incorporated herein by reference (1.8 g, 7.5 mmol) in 10 mL of formic acid was refluxed for 3 h. The reaction mixture was then cooled to ambient temperature and poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 15-25% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.8 g, 90%).

Fuente