Methyl iodide → 2-(4-acetyl-phenylazo)-2-(2,3,3-trimethyl-3,4-dihydro-2H-isoquinoline-1-ylidene)-acetamide

HRID 333634Notes

Reaction equation

HRID 333634 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]([CH3:27])([CH3:26])[NH:17]2)[C:13]([NH2:15])=[O:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:28](=O)([O-])[O-].[Na+].[Na+].CI>C(#N)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]=[N:11][C:12](=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]([CH3:27])([CH3:26])[N:17]2[CH3:28])[C:13]([NH2:15])=[O:14])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 178466770HCID 178466770, compound

Product 1

HCID 729756002-(4-acetyl-phenylazo)-2-(2,3,3-trimethyl-3,4-dihydro-2H-isoquinoline-1-ylidene)-acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-(4-acetyl-phenylazo)-2-(3,3-dimethyl-3,4-dihydro-2H-isoquinoline-1-ylidene) acetamide (Asinex Corp., Russia) and sodium carbonate are added to acetonitrile, and an acetonitrile solution of methyl iodide is slowly dropped and refluxed. The refluxed product is cooled to room temperature and, then, the solvent is removed by reducing a pressure; the residue is dissolved in dichloromethane and washed with distilled water. Thereafter, the product is dried with anhydrous sodium sulfate and filtered and, then, the solvent is removed by reducing the pressure. The residue containing the reaction product is purified by column chromatography to obtain the title compound.

Workup

  1. temperaturerefluxed
  2. customthe solvent is removed
  3. dissolutionthe residue is dissolved in dichloromethane
  4. washwashed with distilled water
  5. dry with materialThereafter, the product is dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed
  8. additionThe residue containing the reaction product
  9. customis purified by column chromatography

Sources & evidence

ORD record
ord-56621459cfc44fc2a624ea0d050e8b77
Source dataset
uspto-grants-2014_11
Patent number
US08883504B2

Reaction notes

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