Phosphorus oxychloride → HCID 18505063, compound

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Reaction Steps

N-(2′-methyl-5′-nitrophenyl)-5-methoxyanthranilic acid (7.2 g) is heated in phosphorous oxychloride (60 ml) at 120° C. for 1 hour. Excess phosphorous oxychloride is distilled off under reduced pressure, and the residue is poured slowly into a stirred mixture of chloroform, concentrated ammonium hydroxide and ice. The separated chloroformic layer is washed with water and dried using magnesium sulfate. Chloroform is evaporated to dryness, and the residue is crystallized from benzene to give 9-chloro-7-methoxy-4-methyl-1-nitroacridine (6.1 g, 68% yield), m.p. 227-228° C. 1H NMR (d6DMSO): δ 8.23 (d, 1H, J=9.3 Hz), 8.13 (d, 1H, J=7.3 Hz), 7.79 (bd, 1H, J=8.3 Hz), 7.71 (dd, 1H, J1=9.3 Hz, J2=2.9 Hz), 7.58 (d, 1H, J=2.9 Hz), 4.02 (s, 3H), 2.85 (s, 3H).

Provenance & Evidence