3,3-dimethyl-1H-quinoline-2,4-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaH (95% in mineral oil, 42 mg, 1.75 mmol) is added carefully to a solution of 3,3-dimethyl-1H-quinoline-2,4-dione (300 mg, 1.58 mmol) in anhydrous THF (10 mL) at 0° C. After 20 min, MeI (269 mg, 1.89 mmol) is added. The resulting mixture is stirred for overnight (˜16 h) at room temperature. Saturated NH4Cl solution is added, the mixture is extracted with ether (20 mL×3). The combined extracts are washed with brine, and dried over anhydrous Na2SO4. After concentration, the title compound is yielded (300 mg, 93% yield). the mixture is extracted with ether (20 mL×3) The combined extracts are washed with brine dried over anhydrous Na2SO4 After concentration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaH (95% in mineral oil, 42 mg, 1.75 mmol) is added carefully to a solution of 3,3-dimethyl-1H-quinoline-2,4-dione (300 mg, 1.58 mmol) in anhydrous THF (10 mL) at 0° C. After 20 min, MeI (269 mg, 1.89 mmol) is added. The resulting mixture is stirred for overnight (˜16 h) at room temperature. Saturated NH4Cl solution is added, the mixture is extracted with ether (20 mL×3). The combined extracts are washed with brine, and dried over anhydrous Na2SO4. After concentration, the title compound is yielded (300 mg, 93% yield). the mixture is extracted with ether (20 mL×3) The combined extracts are washed with brine dried over anhydrous Na2SO4 After concentration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.0 g, 5.2 mmol) and MnO2 (4.5 g, 52 mmol) in DMF-CH2Cl2 (10%, v/v, 20 mL) is heat to reflux for overnight (˜16 h). The insoluble material is removed by filtration through a pad of celite (˜1 cm), and washed with CH2Cl2. The combined solution is concentrated under vacuum, and yields the title compound as colorless solid (675 mg, yield 69%). is heat to reflux for overnight (˜16 h) The insoluble material is removed by filtration through a pad of celite (˜1 cm) washed with CH2Cl2 The combined solution is concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaH (95% in mineral oil, 42 mg, 1.75 mmol) is added carefully to a solution of 3,3-dimethyl-1H-quinoline-2,4-dione (300 mg, 1.58 mmol) in anhydrous THF (10 mL) at 0° C. After 20 min, MeI (269 mg, 1.89 mmol) is added. The resulting mixture is stirred for overnight (˜16 h) at room temperature. Saturated NH4Cl solution is added, the mixture is extracted with ether (20 mL×3). The combined extracts are washed with brine, and dried over anhydrous Na2SO4. After concentration, the title compound is yielded (300 mg, 93% yield). the mixture is extracted with ether (20 mL×3) The combined extracts are washed with brine dried over anhydrous Na2SO4 After concentration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.0 g, 5.2 mmol) and MnO2 (4.5 g, 52 mmol) in DMF-CH2Cl2 (10%, v/v, 20 mL) is heat to reflux for overnight (˜16 h). The insoluble material is removed by filtration through a pad of celite (˜1 cm), and washed with CH2Cl2. The combined solution is concentrated under vacuum, and yields the title compound as colorless solid (675 mg, yield 69%). is heat to reflux for overnight (˜16 h) The insoluble material is removed by filtration through a pad of celite (˜1 cm) washed with CH2Cl2 The combined solution is concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir: