5-Chloro-2-nitroaniline → 5-Methoxy-2-nitroaniline

70 ml of a 28% w/v methanolic solution of sodium methoxide were added at room temperature to a solution of 25 g. of 5-chloro-2-nitroaniline in 500 ml of 1,4-dioxane, and the resulting mixture was heated under reflux for 4 hours, after which the solvent was removed by distillation under reduced pressure. The resulting residue was diluted with water, and the resulting aqueous mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel using a gradient elution method, with mixtures of ethyl acetate and hexane in ratios ranging from 1:4 to 1:2 by volume as the eluent, to give 16.3 g of the title compound, melting at 124°-128° C.

1. temperatureunder reflux for 4 hours
2. customafter which the solvent was removed by distillation under reduced pressure
3. additionThe resulting residue was diluted with water
4. extractionthe resulting aqueous mixture was extracted with ethyl acetate
5. washThe extract was washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over anhydrous sodium sulfate
7. customafter which the solvent was removed by distillation under reduced pressure
8. customThe resulting residue was purified by column chromatography through silica gel using
9. washa gradient elution method

ORD record

ord-9d7027ff06434c86b4382c0bb2206778

Source dataset

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05798375