Reacción #319423

Ecuación de reacción

2-amino-4-chlorobenzoic acid

phosphorous oxychloride

4-phenylcyclohexanone

→

title compound

Rendimiento 70.0%

6,9-Dichloro-1,2,3,4-tetrahydro-2-phenylacridine, hemihydrate

Rendimiento 70.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 3 hours
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue is dissolved in methylene chloride
4. 4
   workup.ADDITIONadded slowly to an ice-NH4OH mixture
5. 5
   workup.STIRRINGThe mixture is stirred for 1/2 hour
6. 6
   Extracciónextracted with methylene chloride
7. 7
   LavadoThe combined extracts are washed with water
8. 8
   Secadodried over Na2SO4
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otroto yield a dark solid

Procedimiento

To a slurry of 15 g (0.0874 mol) of 2-amino-4-chlorobenzoic acid and 150 ml of phosphorous oxychloride is added dropwise 15 g (0.0871 mol) of 4-phenylcyclohexanone. The mixture is stirred at reflux for 3 hours and then concentrated in vacuo. The residue is dissolved in methylene chloride and added slowly to an ice-NH4OH mixture. The mixture is stirred for 1/2 hour and extracted with methylene chloride. The combined extracts are washed with water, dried over Na2SO4, and concentrated in vacuo to yield a dark solid. Trituration with ether provides 20 g (70%) of title compound: m.p. 134°-136° C.; IR 1605, 1585 and 1480 cm-1 ; NMR (CDCl3) δ 8.12-8.0 (m, 2H), 7.54-7.46 (m, 1H), 7.44-7.26 (m, 5H), 3.50-2.88 (m, 5H), and 2.28-2.02 (m, 2H).

Fuente