反应详情

温度

115 °C

A mixture of 83 g of 2-nitro-4-methoxy-5-(3,4-dichlorophenoxy)aniline hydrochloride (0.22 mole) polyphosphoric acid in 250 ml of 85% phosphoric acid was heated in a nitrogen atmosphere at 110-120° C. and 32.17 g of methyl vinyl ketone (0.46 mole) was added dropwise under vigorous stirring. After the addition was complete, the mixture was stirred and maintained at 110-120° C. for a further 4 hours. An additional 14 g of methyl vinyl ketone (0.2 mole) was added and the mixture was heated for a further 4 hours. The reaction mixture was poured into ice cold sodium hydroxide solution (pH 10-12) and left over night. The resulting precipitate was separated by filtration and dried. The solid was dissolved in chloroform and mixed with activated charcoal and filtered through a celite bed. The celite bed was washed with chloroform and the filtrate was concentrated to 400 ml under vacuum and diluted with methanol until a turbidity appeared and left overnight. The crystalline product formed was separated by decantation and crystallized from chloroform to give 8 g of pure product, 5-(3,4-dichlorophenoxy)-6-methoxy-4-methyl-8-nitroquinoline. The combined filtrates were evaporated to dryness and the residue was chromatographed over silica gel with 30% chloroform in hexane to yield a fraction from which the product which was crystallized (chloroform/methanol) to give 13 g of product.

1. additionAfter the addition
2. temperaturemaintained at 110-120° C. for a further 4 hours
3. temperaturethe mixture was heated for a further 4 hours
4. waitleft over night
5. customThe resulting precipitate was separated by filtration
6. customdried
7. dissolutionThe solid was dissolved in chloroform
8. additionmixed with activated charcoal
9. filtrationfiltered through a celite bed
10. washThe celite bed was washed with chloroform
11. concentrationthe filtrate was concentrated to 400 ml under vacuum
12. additiondiluted with methanol until a turbidity
13. customThe crystalline product formed
14. customwas separated by decantation
15. customcrystallized from chloroform