Ethyl bromoacetate → HCID 24823447, compound

Temperature

-78 °C

To a solution of 3,4-dihydro-6-methoxy-1(2H)-isoquinolinone (852 mg, 4.81 mmol, prepared according to J. Chem. Soc., 1969, p 183) in THF (45 mL) at −78° C. was added 0.5M potassium hexamethyldisilazide (10.6 mL, 5.28 mmol) dropwise and the reaction mixture stirred at −78° C. for 5 minutes. The reaction mixture was warmed to 0° C. in a ice/water bath and ethyl bromoacetate (1.20 g, 7.21 mmol) was added dropwise and the mixture stirred at that temperature for 1 hour, and then at room temperature for 2 hours. The reaction mixture was quenched by addition of sat. NaHCO3, diluted with ethyl acetate, and the organic layer was washed with saturated NaHCO3 and then brine. It was dried (MgSO4) and concentrated in vacuo to afford the title compound (1.1 g, 86%) as a yellow solid. Molecular weight (MS): 263.

1. temperatureThe reaction mixture was warmed to 0° C. in a ice/water bath
2. stirringthe mixture stirred at that temperature for 1 hour
3. waitat room temperature for 2 hours
4. customThe reaction mixture was quenched by addition of sat. NaHCO3
5. additiondiluted with ethyl acetate
6. washthe organic layer was washed with saturated NaHCO3
7. dry with materialIt was dried (MgSO4)
8. concentrationconcentrated in vacuo

ORD record

ord-647f5e717d4e45589042c33e201e766b

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06664250B2