Phosphorus oxychloride → 4-Chloro-6-fluoro-3-nitro-quinoline

Participants

Reaction Conditions

Reaction Steps

2.3 g (11 mmol) of 6-fluoro-3-nitro-quinolin-4-ol (Example 19b) in 12 ml POCl3 are heated kept at 130° C. for 4 h. The reaction mixture is cooled to 0° C. and poured into ice-water. A precipitate is formed, which is filtered off and washed with water. The solid material is dissolved in CH2Cl2 and washed with 0.1N NaOH and water. After drying the organic phase over MgSO4, the solvent is evaporated to dryness. The residue is dissolved in a few ml of CH2Cl2 and hexane is added. The title compound precipitates and is filtered off. Drying is done at 60° C. (high-vacuum) overnight. NMR (DMSO-d6): 9.38/s (1H), 8.32/d×d (1H), 8.18/d×d (1H) and 8.02/d×t (1H); HPLC: tret=11.82 min (Grad 1).

Provenance & Evidence