Reacción #1132544

Ecuación de reacción

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

methyl iodide

cesium carbonate

→

4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

Rendimiento 85.3%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was irradiated by microwave at 100° C. for 30 minutes
2. 2
   OtroThe solvent was removed
3. 3
   Lavadothe residue was washed with water
4. 4
   Extracciónextracted with dichloromethane
5. 5
   OtroPurification by silica chromatography (ISCO)

Procedimiento

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.5 g, 2.82 mmol), methyl iodide (0.6 g, 4.23 mmol) and cesium carbonate (1.37 g, 4.23 mmol) were dissolved in dry dimethylformamide (2 mL). The reaction mixture was irradiated by microwave at 100° C. for 30 minutes. The solvent was removed and the residue was washed with water and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.46 g, 85%). 1H NMR (400 MHz, DMSO-d6): δ 9.95 (s, 1H), 7.62 (s, 1H), 7.59 (d, 1H), 7.20 (d, 1H), 4.80 (s, 2H), 3.34 (s, 3H); MS (ESI) m/z: Calculated for C10H9NO3: 191.1. found: 192.1 (M+H)+.

Fuente