Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][CH:5]=1.N([O-])=O.[Na+].[CH:15](=[O:21])[C:16]1[O:20][CH:19]=[CH:18][CH:17]=1>O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:19]2[O:20][C:16]([CH:15]=[O:21])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1A 5l. three-necked flask equipped with stirrer, thermometer and dropping funnel was charged with water (150ml), concentrated HCl (400 ml) was introduced, followed by p-anisidine (185 g, 1.5 moles). A solution of sodium nitrite (108 g, 1.56 moles) in water (300 ml) was introduced dropwise maintaining -10° to -5°C. Furfural (184 g, 1.92 moles) was introduced followed by a solution of CuCl2.2H2O (46 g) in water (300 ml). The reaction mixture was heated to 53° with hot water maintaining 53°-68° for 2.5 hours. After cooling to room temperature overnight, the reaction mixture was extracted with ether (1800 ml). The dried (MgSO4) extract was evaporated in a rotary evaporator, and the residue was distilled under reduced pressure to give 70 g of black semi-solid product (b.p. 160°-190° at 2-5 mm).
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