P-Anisidine → HCID 70691178, compound

Participants

Reaction Steps

2,4-Dichloro-1,5-dinitrobenzene (II-1, 0.5 g, 2.11 mmol) and p-methoxyaniline (III-2, 0.2 g, 2.11 mmol) were dissolved in 5 mL DMSO. To the solution were added K2CO3 (0.58 g, 4.22 mmol) and metal Cu in catalytic amount. The mixture was allowed to react at 115° C. for 2 hours with stirring in an atmosphere of nitrogen. The resultant was poured into ice water, stirred to precipitate a solid. The solid was filtered, washed with water several times, dried, and separated on silica gel column (petroleum ether/ethyl acetate) to obtain a bronzing solid (IV-2, 0.68 g, 67%). 1H NMR (CDCl3) δ ppm 3.88 (3H, s, OCH3), 7.02 (1H, s, ArH-6), 7.03 (2H, d, J=8.96 Hz, ArH-3′, 5′), 7.21 (2H, d, J=8.96 Hz, ArH-2′, 6′), 9.07 (1H, s, ArH-3), 9.73 (1H, s, NH).

Provenance & Evidence