Potassium Carbonate → 7-Ethynyl-4,4-dimethyl-1-(propan-2-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 52451Notes

Reaction equation

HRID 52451 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[N:5]([CH:18]([CH3:20])[CH3:19])[C:4](=[O:21])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:22][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([CH:18]([CH3:19])[CH3:20])[C:4](=[O:21])[CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 199637194,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-[(trimethylsilyl)ethynyl]quinoline2×

Product 1

HCID 199637207-Ethynyl-4,4-dimethyl-1-(propan-2-yl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-[(trimethylsilyl)ethynyl]quinoline (Compound 29) in 7.0 ml of methanol was added potassium carbonate. The mixture was stirred at room temperature for 10 h. The reaction mixture was then concentrated in vacuo and the resulting oil was dissolved in water, and extracted using methylene chloride (2×). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe resulting oil was dissolved in water
  3. extractionextracted
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48ed3ed068b34df08874ebd65bf61edd
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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