Nitromethane → HCID 11127094, compound

Temperature

0 °C

1 g of AlCl3 were suspended in 10 ml DCM, 0.5 ml of nitromethane were added to dissolve AlCl3, and the solution was cooled to 0° C. 4-Methyl-4H-benzo[1,4]oxazin-3-one (0.5 g, 3.06 mmol) dissolved in DCM was added to the above solution and stirred for 15 minutes at 0° C. To this solution was further added 0.36 ml of bis-chloromethyl-methylether in DCM. The reaction was stirred at 0° C. for 15 minutes and at room temperature for 3 h. The crude reaction mixture was then poured onto ice, the layers were separated and the organic phase was washed with NaHCO3 and brine. After drying over MgSO4 and filtration the solvent was evaporated, which afforded 0.43 g of crude product. The dark oil was purified by flash chromatography using EtOAc and cyclohexane as eluents, affording 0.2 g (37%) of 4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde as colourless solid.

1. additionwas added to the above solution
2. stirringThe reaction was stirred at 0° C. for 15 minutes and at room temperature for 3 h
3. customThe crude reaction mixture
4. additionwas then poured onto ice
5. customthe layers were separated
6. washthe organic phase was washed with NaHCO3 and brine
7. dry with materialAfter drying over MgSO4 and filtration the solvent
8. customwas evaporated
9. customwhich afforded 0.43 g of crude product
10. customThe dark oil was purified by flash chromatography

ORD record

ord-c63fb894e621493cac7c5d3b8c6fdce6

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846925B2