Methyl iodide → 2,4-Quinolinedione, 1,2,3,4-tetrahydro-1,3,3-trimethyl-

HRID 1097778Notes

Reaction equation

HRID 1097778 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:16])[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:15].[CH3:17]I.[NH4+].[Cl-]>C1COCC1>[CH3:17][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[C:4]([CH3:16])([CH3:3])[C:5]1=[O:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 138366743,3-Dimethylquinoline-2,4(1H,3H)-dione

Product 1

HCID 992162,4-Quinolinedione, 1,2,3,4-tetrahydro-1,3,3-trimethyl-Yield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. extractionthe mixture is extracted with ether (20 mL×3)
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-33e1a3fba36f435c9e261b99b29907e6
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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