2H-1,4-Benzoxazin-3(4H)-one,4-methyl- → 2H-1,4-Benzoxazine, 3,4-dihydro-4-methyl-

To a stirred solution of 4-methyl-4H-benzo[1,4]oxazin-3-one (2.18 g, 13.37 mmol) in THF (5 mL) was added borane-tetrahydrofuran complex (4.02 g, 46.8 mmol) at room temperature. After stirring the solution for 2 h, the reaction mixture was refluxed for 4 h. After complete conversion, reaction mixture was quenched by adding MeOH (10 mL) and evaporated the solvents. The residue obtained was extracted with ethyl acetate (30×2 mL) and the organic layer was washed with water (20 mL), brine (20 mL) and evaporation of solvent gave 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine 2.0 g.

1. temperaturethe reaction mixture was refluxed for 4 h
2. customAfter complete conversion, reaction mixture
3. customwas quenched
4. additionby adding MeOH (10 mL)
5. customevaporated the solvents
6. customThe residue obtained
7. extractionwas extracted with ethyl acetate (30×2 mL)
8. washthe organic layer was washed with water (20 mL), brine (20 mL) and evaporation of solvent

ORD record

ord-0165b565e08449a89ac8f06d349cbf4e

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828951B2