Triethylsilane → 6-Ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1184437Notes

Reaction equation

HRID 1184437 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

HCID 12052TriethylsilaneHCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 508787336-Ethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with sat aqueous NaHCO3
  3. customthe resulting solid was isolated by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give a white solid

Sources & evidence

ORD record
ord-6c6accc229be4d0cbc7dae2beb566d66
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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