Methyl iodide → HCID 58495141, compound

HRID 516226Notes

Reaction equation

HRID 516226 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12][C:7]=3[CH:8]=2)[NH:3]1.[H-].[Na+].CI.[C:26](=O)([O-])O.[Na+]>CN(C=O)C>[CH3:26][N:3]1[C:4]2[C:9](=[CH:8][C:7]3[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:16][C:6]=3[CH:5]=2)[CH2:10][CH2:11][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66982390HCID 66982390, compound

Product 1

HCID 58495141HCID 58495141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

287 mg of ethyl 2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate was dissolved in 5 ml of DMF, and 65 mg of 60% sodium hydride was added thereto in an ice-bath, followed by stirring for 1 hour. 0.3 ml of methyl iodide was added thereto, followed by stirring at room temperature for 3 hours. Then, a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform. The solvent was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 94 mg of ethyl 1-methyl-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a colorless solid.

Workup

  1. customin an ice-bath, followed
  2. stirringby stirring at room temperature for 3 hours
  3. extractionfollowed by extraction with chloroform
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-5ec0131dd5cb4fe489f5582ad2e3d3a6
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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