Methyl iodide → Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-

HRID 1242921Notes

Reaction equation

HRID 1242921 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[H-].[Na+].[CH3:18]I>O1CCCC1>[CH3:18][N:4]([C:5]1[CH:14]=[CH:13][C:12]2[C:11](=[O:15])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=1)[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 10536752Acetamide, N-methyl-N-(5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Acetamido-1-tetralone (10.0 g, 49.2 mmol) was dissolved in tetrahydrofuran (100 ml). Sodium hydride (oil, 3.0 g) was added to the solution, which was refluxed with heating under nitrogen atmosphere for 2 hours. After cooling, methyl iodide (30 ml) was added to the reaction mixture, which was refluxed with heating under nitrogen atmosphere for 2 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue, and extraction was conducted. The ethyl acetate layer was concentrated, and the residue was purified by alumina column chromatography (development solvent; ethyl acetate: n-hexane=33:67˜50:50). The product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate diisopropyl ether, to give the titled compound (4.3 g).

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating under nitrogen atmosphere for 2 hours
  3. temperatureAfter cooling
  4. temperaturewas refluxed
  5. temperaturewith heating under nitrogen atmosphere for 2 hours
  6. concentrationThe reaction mixture was concentrated
  7. additionEthyl acetate and water were added to the residue, and extraction
  8. concentrationThe ethyl acetate layer was concentrated
  9. customthe residue was purified by alumina column chromatography (development solvent; ethyl acetate: n-hexane=33:67˜50:50)
  10. concentrationThe product was concentrated under reduced pressure
  11. customthe residue was recrystallized from ethyl acetate diisopropyl ether

Sources & evidence

ORD record
ord-b08334265d614a12aeeea10195a80219
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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