Methyl iodide → Nitrobenzene

1.00 g (4.29 mmole) of 4-(3-methylbutylamino)-3-nitrobenzonitrile was dissolved in 10 mL of DMF, 0.205 g (5.14 mmoles) of NaH was added, and the mixture was stirred for 10 minutes at room temperature. 0.5 mL (5.14 mmole) of methyl iodide was added and the mixture was stirred overnight at room temperature. When the reaction had ended, the solvent was removed under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate. The residue was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure, yielding a nitrobenzene intermediate. Next, the nitrobenzene intermediate was dissolved in 20 mL of ethanol, 50 percent NH2OH aqueous solution was added, and the mixture was stirred overnight at 50° C. When the reaction had ended, the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography, yielding 1.46 g of amideoxime intermediate.

1. stirringthe mixture was stirred overnight at room temperature
2. customthe solvent was removed under reduced pressure, and water
3. additionwas added to the residue
4. extractionThe mixture was extracted with ethyl acetate
5. washThe residue was washed with saturated brine
6. dry with materialdried with anhydrous sodium sulfate
7. customThe solvent was removed under reduced pressure

ORD record

ord-0f9c7a2664d14111891d131eb53b3168

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402696B2