N,O-Dimethylhydroxylamine → 3,N-Dimethoxy-N-methyl-5-trifluoromethylbenzamide

Temperature

-15 °C

Methyl 3-methoxy-5-trifluoromethylbenzoate (O4.014, 1 g) and N,O-dimethylhydroxylamine (416 mg) were initially charged in THF (30 ml). Thereafter, the mixture was cooled to −15° C., and isopropylmagnesium chloride (3.2 ml; 2 M in THF) was added dropwise within 10 min. The mixture was stirred at −15° C. for another 20 min before the cooling bath was removed. After 3 h, the mixture was cooled again to −15° C. and further isopropylmagnesium chloride (3.2 ml) was added. After the cooling bath had been removed, the mixture was stirred at RT for another hour, then admixed with 20% ammonium chloride solution and extracted three times with EA. The combined EA phases were dried over sodium sulfate, filtered and concentrated. The residue was purified using silica gel (50 g cartridge, DCM as eluent). 465 mg of the title compound were obtained, as well as 427 mg of reactant.

1. customwas removed
2. waitAfter 3 h
3. temperaturethe mixture was cooled again to −15° C.
4. additionfurther isopropylmagnesium chloride (3.2 ml) was added
5. customAfter the cooling bath had been removed
6. stirringthe mixture was stirred at RT for another hour
7. extractionextracted three times with EA
8. dry with materialThe combined EA phases were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified

ORD record

ord-1062796471184d87b25a896acc16166a

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076336B2