Methyl iodide → 2-Methyl-1,2,4,5-tetrahydro-benzo[c]azepin-3-one

HRID 1688108Notes

Reaction equation

HRID 1688108 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][C:5](=[O:14])[NH:4]1.[CH3:15]I>C1COCC1>[CH3:15][N:4]1[C:5](=[O:14])[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 28330792,3,4,5-tetrahydro-1H-2-benzazepin-3-one

Product 1

HCID 109100902-Methyl-1,2,4,5-tetrahydro-benzo[c]azepin-3-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 25° C., sodium hydride (150 mg, 6.3 mmol) was added to a solution of 1,2,4,5-tetrahydro-benzo[c]azepin-3-one (1 g, 6 mmol) in THF (50 mL). The suspension was stirred for 10 minutes and treated with methyl iodide (1 g, 7 mmol). The mixture was stirred for an additional 4 hours and then partitioned between ethyl acetate (100 ml) and water (50 ml). Washing once with brine (30 ml), drying over anhydrous magnesium sulfate and evaporation of solvent gave 2-methyl-1,2,4,5-tetrahydro-benzo[c]azepin-3-one (1 g, 5.7 mmol, 95%): 1H NMR (300 MHz, CDCl3) δ 7.2 (m, 5H), 4.52 (s, 2H), 3.18 (t, 2H), 3.09 (s, 3H), 3.00 (t, 2H).

Workup

  1. stirringThe mixture was stirred for an additional 4 hours
  2. custompartitioned between ethyl acetate (100 ml) and water (50 ml)
  3. washWashing once with brine (30 ml)
  4. dry with materialdrying over anhydrous magnesium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-abaaa25dc92648a1905c77cb55c6e13e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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