Methyl iodide → 3-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one

HRID 2376614Notes

Reaction equation

HRID 2376614 reaction equation
[H-].[Na+].[CH2:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][NH:5][C:4]1=[O:14].[CH3:15]I>CN(C=O)C>[CH3:15][N:5]1[C:4](=[O:14])[CH2:3][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2042322H-3-Benzazepin-2-one, 1,3,4,5-tetrahydro-

Product 1

HCID 8521743-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride (1.1 eq) in 15 mL of dry DMF was added 2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (0.0042 moles) as a solution in 10 mL of DMF. Methyl iodide (about 2 eq.) was then added. When complete by TLC, the reaction mixture was poured over ice and extracted into ethyl acetate. The organic layer was washed with water, followed by brine. The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by HPLC (LC 2000), eluting with an ethyl acetate/hexane system to give 3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one.

Workup

  1. additionWhen complete by TLC, the reaction mixture was poured over ice
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC (LC 2000)
  8. washeluting with an ethyl acetate/hexane system

Sources & evidence

ORD record
ord-3e95c5fb9ff248e8a3e56909e59384e2
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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