Ammonium Hydroxide → 2,7-Dichloro-4-methylquinoline

Participants

Reaction Steps

A solution of quinolone 13 (10 g; 51.6 mmol) in 90 ml of POCl3 was refluxed for 2 hours. After cooling, the mixture was poured into 300 g ice-water and neutralized with NH4OH. The resultant precipitate was filtered off and washed with cold H2O. The crude product was recrystallized from 95% ethanol to obtain 8.95 g (72%) of 14. 1H NMR (CDCl3): δ 2.71 (s, 3H); 7.28 (d, 1H); 7.55 (d, 1H); 7.92 (d, 1H); 8.08 (d, 1H).

Provenance & Evidence