Phosphorus oxychloride → 9-Chloro-1,2,3,4-tetrahydroacridine
Reaction equation
[C:1]1(=[N:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][C:10]1[C:9]2[C:8]([N:7]=[C:1]3[C:6]=1[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:16][CH:15]=[CH:14][CH:13]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-Cyclohexylideneamino-benzoic acid (1.5 g, 6.9 mmol) was added to phosphorus oxychloride (4 mL) at 0° C. and stirred for 5 minutes followed by heating to 100° C. for 45 minutes. The reaction mixture was cooled to room temperature and slowly poured onto ice (˜100 g) and stirred for 30 minutes. CH2Cl2 (100 mL) was added and the mixture stirred for 5 minutes and the organic layer separated. The aq. layer was extracted with CH2Cl2 (50 mL). The combined CH2Cl2 layers were washed with sat. aq. NaHCO3 (2×50 mL), sat. aq. NaCl (50 mL), dried over Na2SO4, decanted and concentrated to give 9-chloro-1,2,3,4-tetrahydro-acridine, which, was used without further purification.