Ammonium Hydroxide → 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Participants

Reaction Steps

A mixture of N-(1-ethyl-3-methylpyrazol-5-yl) anthranilic acid (7.0 g), 28.57 mmol) and POCl3 (210 ml) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, poured into ice-water and neutralized with concentrated NH4OH to a pH of 8.0. The product which slowly crystallized from the solution was collected by filtration, washed with water and dried to afford 6.7 g (95%) of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline.

Provenance & Evidence