反应详情

温度

47 °C

To a stirred mixture of 30.0 ml of acetic anhydride and 15.0 ml of glacial acetic acid there was added gradually 5.0 g of 2-(4-dimethylaminophenyl)carbonyl-5-dimethylaminobenzoic acid. The reaction mixture was heated slowly to approximately 47° C. and maintained at a temperature in the range of 45° to 50° C. for approximately thirty minutes. The resultant mixture was cooled to ambient temperature, stirred approximately forty-five minutes and then cooled to approximately 0° C. A solution of 15.0 ml of methyl alcohol and 19.4 ml of pyridine was added dropwise to the reaction mixture while maintaining a temperature of approximately 0° C. The resulting mixture was allowed to stir at ambient temperature for approximately two hours. After adding toluene to the reaction mixture, five percent aqueous ammonium hydroxide, was added slowly until the resulting mixture was slightly alkaline. The toluene layer was separated from the alkaline water layer and toluene was removed under reduced pressure to obtain 4.67 g of 3-methoxy-3-(4-dimethylaminophenyl)-6 -dimethylaminophthalide (Formula II: R0 =R=R2 =R5 =H; R1 =N(CH3)2 ; R4 =R4' =Y=CH3 ; X=O), a pale green-colored solid which melted at 140° to 147° C. A significant infrared maximum appeared at 1760 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. A toluene solution of the product spotted on an acid-clay coated paper developed a turquoise-colored image.

1. temperaturemaintained at a temperature in the range of 45° to 50° C. for approximately thirty minutes
2. temperaturecooled to approximately 0° C
3. temperaturewhile maintaining a temperature of approximately 0° C
4. stirringto stir at ambient temperature for approximately two hours
5. additionwas added slowly until the resulting mixture
6. customThe toluene layer was separated from the alkaline water layer and toluene
7. customwas removed under reduced pressure