Triethylsilane → 6-Ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one
Reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)(=O)[CH3:2].[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[CH2:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 6-Acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one (14) (0.5 mmol) in TFA (4 mL) was added Et3SiH (1.0 mmol). The reaction was heated at 80° C. for 2 h and then concentrated in vacuo. The residue was treated with sat aqueous NaHCO3 and the resulting solid was isolated by filtration, washed with water and dried in vacuo to give a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.63 (s, 1H), 6.81-6.87 (m, 1H), 6.71 (s, 1H), 6.74 (d, J=8.1 Hz, 1H), 4.51 (s, 2H), 2.46-2.54 (m, 2H), 1.12 ppm (t, J=7.6 Hz, 3H). ESI-MS: m/z 178.0 (M+H)+.