Ammonium Chloride → HCID 118093669, compound

Temperature

0 °C

To a solution of 4-bromo-5-(cyclobutylmethoxy)-2-nitroaniline (1.027 g, 3.410 mmol) ion 1:1 EtOAc/MeOH (40. mL) was added saturated aqueous solution of NH4Cl (3.0 mL). The suspension was cooled to 0° C. using an ice bath, and zinc powder (1.8 g, 28 mmol) was added in three portions over 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was then warmed to 55° C., and the reaction mixture was stirred for an additional 1 h at that temperature. The reaction mixture was diluted with EtOAc and filtered through Celite. The filter cake was washed with EtOAc. The filtrate was washed with saturated aqueous solution of NaHCO3 (100 mL) and then brine (100 mL). The resulting organic layer was dried over Na2SO4, filtered, and concentrated to afford a purple oil (1.017 g, >99%). LCMS calculated for C11H15BrN2O (M+H)+: m/z=271.0, 273.0. found: 271.0, 273.0.

1. temperatureto warm to room temperature
2. temperatureThe reaction mixture was then warmed to 55° C.
3. stirringthe reaction mixture was stirred for an additional 1 h at that temperature
4. filtrationfiltered through Celite
5. washThe filter cake was washed with EtOAc
6. washThe filtrate was washed with saturated aqueous solution of NaHCO3 (100 mL)
7. dry with materialThe resulting organic layer was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-62557390c5774bfca41592e9f5435ad6

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315501B2