反应详情

To a stirred solution of 2-chloro-3-nitrobenzoic acid (6.0 grams, 0.031 mole) in toluene (100 mL) was added thionyl chloride (6.8 mL, 0.092 mole). Upon completion of addition, the reaction mixture was heated to reflux where it stirred for four hours. After this time, the reaction mixture was filtered and concentrated. The concentrate was taken up in ether and added dropwise to an ice-cold solution of N-methylhydroxylamine hydrochloride (2.6 g, 0.031 mole), sodium bicarbonate (5.5 g, 0.065 mole), water (20 mL), and ether (160 mL). Upon completion of addition, the reaction mixture was stirred for one hour. After this time, the reaction mixture was diluted with water and the ether layer was separated. The aqueous layer was extracted twice with ether. The combined ether layer and extracts were dried over magnesium sulfate and concentrated to provide 6.4 grams of N-methyl-N-hydroxy-2-chloro-3-nitrobenzamide. The NMR spectrum was consistent with the proposed structure.

1. additionUpon completion of addition
2. temperaturethe reaction mixture was heated
3. temperatureto reflux where it
4. filtrationAfter this time, the reaction mixture was filtered
5. concentrationconcentrated
6. additionUpon completion of addition
7. stirringthe reaction mixture was stirred for one hour
8. customthe ether layer was separated
9. extractionThe aqueous layer was extracted twice with ether
10. dry with materialThe combined ether layer and extracts were dried over magnesium sulfate
11. concentrationconcentrated