Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59436282, compound

Temperature

0 °C

To a stirred suspension of N,O-dimethylhydroxylamine hydrochloride (0.468 g, 4.8 mmol) in dichloromethane (5 mL) was added trimethylaluminum (2.4 mL, 4.8 mmol, 2 M solution in toluene) dropwise at 0° C. Following addition, the suspension was stirred at 0° C. for 10 min then at room temperature for 30 min to provide a homogenous solution. The flask was then re-cooled in an ice bath. In a separate flask, methyl 5-methyl-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylate (0.500 g, 1.6 mmol) was dissolved in dichloromethane (5 mL) and added dropwise and allowed to stir for 2 h. The reaction was quenched with water (5 mL) and 2 N HCl aqueous solution (2 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to provide N-methoxy-N,5-dimethyl-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (0.535 g, 98%) as a yellow solid.

1. additionaddition
2. customat room temperature for 30 min to provide a homogenous solution
3. temperatureThe flask was then re-cooled in an ice bath
4. additionadded dropwise
5. stirringto stir for 2 h
6. customThe reaction was quenched with water (5 mL) and 2 N HCl aqueous solution (2 mL)
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
9. washThe combined organic extracts were washed with brine (20 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-9bef8c7adfd049a2b8827bad9f12038c

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354411B2