and 3 ml 28 ammonium hydroxide after filtration the reaction mixture is washed with water and extracted with 10 hcl the extract is washed with ether and then basified with 28 nh 4 oh the basic solution is extracted with ether the ether extract is washed with saturated nacl solution dried over na 2 so 4 and evaporated to dryness the resulting oil is purified by chromatography to give a yellow solid m p 132 u00b0 134 u00b0 c analysis calcd for c 22 h 25 n 4 c 69 37 h 6 62 n 14 71 found c 69 09 h 6 62 n 14 53 in a 3 liter three necked round bottom flask provided with a mechanical stirrer reflux condenser and thermometer to 200 u00b0 c was placed 300 g 1 25 m 1 bromo 4 chloronitrobenzene 140 g 1 02 m anthranilic acid and 130 ml n amyl alcohol the mixture was heated in an oil bath after most of the chemicals were dissolved 80 u00b0 90 u00b0 c the stirrer was started then 1 3 gm copper powder and 140 gm 1 02 m potassium carbonate were added all at once a yellow voluminous froth formed but no heat of reaction as the reaction temperature rose from 180 u00b0 to 120 u00b0 a red reaction mixture became more solid and hindered further stirring the reflux condenser was replaced to distill off the formed water and amyl alcohol meanwhile the temperature of the oil bath was steadily increased and finally kept at 200 u00b0 210 u00b0 for 3 hours the oil bath was replaced by a steam bath and the excess bromochloronitrobenzene was removed by steam distillation after removal of bromochloronitrobenzene was completed the solution was filtered and water.