Isopropyl iodide → HCID 15338266, compound

HRID 1440428Notes

Reaction equation

HRID 1440428 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1.[CH:16](I)([CH3:18])[CH3:17]>CN(C=O)C>[CH:16]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:15])([CH3:3])[CH2:5][C:6]1=[O:14])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one2×

Product 1

HCID 15338266HCID 15338266, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.121 g, 3.0 mmol) in dry DMF (2 mL) was added a solution of 4,4,-dimethyl-2-oxoquinoline (Compound 38, 0.529 g, 3.0 mmol) in dry DMF (10 mL). The mixture was stirred at room temperature for 30 min followed by addition of isopropyl iodide. The reaction mixture was left at room temperature for 72 h. Then ice-cubes were added to the reaction and the mixture was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with saturated solution of NaCl, dried over MgSO4 and concentrated to give a pale yellow oil. Purification by column chromatography (silica gel, 30% ethyl acetate in hexane) yielded the title compound as a colorless oil (472 mg, 72%). 1H NMR d 1.32 (s, 6H), 1.57 (d, J=7.1 Hz, 6H), 2.45 (s, 2H), 4.74 (q, J=7.0 Hz, 1H), 7.06-7.32 (m, 4H).

Workup

  1. waitThe reaction mixture was left at room temperature for 72 h
  2. additionThen ice-cubes were added to the reaction
  3. extractionthe mixture was extracted with ethyl acetate (2×5 mL)
  4. washThe combined organic layers were washed with saturated solution of NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a pale yellow oil
  8. customPurification by column chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7e3a5a26254341d2b39d4412d75da514
Source dataset
uspto-grants-1996_03
Patent number
US05498755

Reaction notes

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