Methyl iodide → 1-methyl-8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 518845Notes

Reaction equation

HRID 518845 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:17]=[CH:16][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:15])[NH:14][C:8]=2[CH:7]=1)([O-:5])=[O:4].I[CH3:19]>CN(C=O)C>[CH3:19][N:14]1[C:8]2[CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:17]=[CH:16][C:9]=2[CH2:10][CH2:11][CH2:12][C:13]1=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 40932148-Nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 197602341-methyl-8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

144 mg of NaH (50%) are added to a solution of 549 mg of 8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 15 ml of DMF. The reaction medium is stirred for 15 minutes and then 187 μl of iodomethane are added. The mixture is stirred for 16 hours at ambient temperature and then run into ice-cold water and extracted with ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is taken up in diisopropyl ether and the insoluble material is filtered off and dried under vacuum, so as to give 405 mg of 1-methyl-8-nitro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of a beige solid.

Workup

  1. stirringThe mixture is stirred for 16 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe insoluble material is filtered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b6bdb8e60a454b369e50a6024c4a041c
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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