Phosphorus oxychloride → HCID 19592216, compound

Participants

Reaction Steps

A mixture of N-(1-isopropylpyrazol-5-yl) anthranilic acid (52 g, 0.212 mol) and POCl3 (436 ml, 4.68 mol) is refluxed for 3 hours, then is stirred at room temperature overnight. The excess POCl3 is removed by distillation and then the residue is poured into ice/water. The mixture is neutralized with 35% NaOH and then extracted with CH2Cl2. The CH2Cl2 layer is separated and washed with water, then brine and then is dried over MgSO4, filtered and evaporated. The residue is dissolved in CH2Cl2 and then is purified by column chromatography on silca gel eluting with CH2Cl2 to afford 21.3 g (40.9%) of 1-isopropyl-4-chloro-1H-pyrazolo[3,4-b]quinoline.

Provenance & Evidence