4-Methyl-3-nitrobenzoic acid → N'-acetyl-4-methyl-3-nitrobenzohydrazide

4-Methyl-3-nitrobenzoic acid (3.00 g, 16.5 mmol) was added to dichloromethane (50 ml), triethylamine (3.0 ml, 21.3 mmol) and isobutyl chloroformate (2.80 ml, 21.5 mmol) were added under ice-cooling with stirring, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was ice-cooled again, acetohydrazide (2.45 g, 33.1 mmol) was added with stirring, and the mixture was stirred at room temperature for about 3 hr. The reaction mixture was diluted with ethyl acetate, washed with 10% aqueous citric acid solution, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with diethyl ether and hexane to give the title compound (1.72 g, yield 44%) as a colorless solid.

1. additionwere added under ice-
2. temperaturecooling
3. stirringthe mixture was stirred at room temperature for 3 hr
4. temperaturecooled again
5. stirringwith stirring
6. stirringthe mixture was stirred at room temperature for about 3 hr
7. washwashed with 10% aqueous citric acid solution
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationThe insoluble material was filtered off
10. concentrationthe solution was concentrated under reduced pressure
11. washThe obtained solid was washed with diethyl ether and hexane

ORD record

ord-d2f3d1d6ab56494f99ed263bf1728d3b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2