Methyl iodide → HCID 136207705, compound

HRID 361615Notes

Reaction equation

HRID 361615 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][C:5]=1[C:15]([O:17][CH3:18])=[O:16].CI.[C:21](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][O:1][N:2]=[CH:3][C:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[NH:6][C:5]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136365331HCID 136365331, compound

Product 1

HCID 136207705HCID 136207705, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.8 g (3.25 mmol) of methyl 3-(hydroxyiminomethyl)-4,7-dimethylindole-2-carboxylate, 0.60 g (4.23 mmol) of methyl iodide, 0.59 g (4.23 mmol) of potassium carbonate and 20 ml of acetonitrile was refluxed for 19 hours. After potassium carbonate was removed by filtration, acetonitrile was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water three times and dried over anhydrous magnesium sulfate. The crude crystals were purified by silica gel column chromatography to provide 210 mg of light yellow crystals. Yield: 25%

Workup

  1. temperaturewas refluxed for 19 hours
  2. customAfter potassium carbonate was removed by filtration, acetonitrile
  3. distillationwas distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water three times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe crude crystals were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6451de8f802942398b6ac7cb6ee539c8
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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