Phosphorus oxychloride → HCID 57437660, compound

Reaction equation

[CH3:1][C:2]1[C:15]2[C:6](=[CH:7][N:8]=[C:9]3[C:14]=2[C:13](=O)[CH2:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:18].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:18][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:6]=1[CH:5]=[CH:4][CH:3]=[C:2]3[CH3:1])[CH:13]=[CH:12][CH:11]=[CH:10]2

Participants

Procedure

The above compound, 10-methyl-phenanthridinone (4.0 grams, 19 mmole) was added to a reaction flask containing phosphorus pentachloride (6.0 grams, 0.29 mole) and phosphoryl chloride (50 mL). The reaction mixture was refluxed for 4 hours, cooled to room temperature and diluted with toluene. The excess phosphoryl chloride and toluene were removed by a rotary evaporator. The residue was dissolved into ethyl acetate and washed with distilled water followed by brine. The solvent layer was dried over magnesium sulfate, filtered and concentrated to give 6-chloro-10-methylphenanthridine (4.1 grams, 95%) as an off-white solid. The product was confirmed by Mass Spec and NMR and not purified further but used directly in the next step.