Phosphorus oxychloride → 4-Chloro-3-nitroquinoline

Participants

Reaction Steps

5.5 g (29 mmol) 3-nitro-quinolin-4-ol (Example 1a) in 25 ml POCl3 are heated for 2 h to keep at 130° C. The mixture is cooled to rt and poured into ice-water. The precipitate is filtered off, washed with ice-cold water, and dissolved in CH2Cl2. The organic phase is washed with cold 0.1N NaOH (1×) and with cold water (2×). After drying over MgSO4, the solvent is evaporated to dryness. The residue is stirred in hexane. The title compound is isolated as a powder and is dried at 60° C. under vacuum. mp: 121-122° C.; NMR (CDCl3): 9.26/s (1H), 8.44/d and 8.21/d (2H), 7.95/t and 7.82/t (2H); HPLC: tret=1 1.64 min (Grad 1).

Provenance & Evidence