Methyl iodide → HCID 19592927, compound

HRID 613531Notes

Reaction equation

HRID 613531 reaction equation
[C:1]([CH2:4][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16](=[O:25])[C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[CH2:26][CH3:27])([OH:3])=[O:2].[C:28](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=1[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([CH2:26][CH3:27])=[C:5]2[CH2:4][C:1]([O:3][CH3:28])=[O:2])=[O:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19592326HCID 19592326, compound

Product 1

HCID 19592927HCID 19592927, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-carboxymethyl-8-(2,6-dichlorobenzoylamino)-3-ethylquinoline (405 mg) in dimethylformamide were added potassium carbonate (305 mg) and methyl iodide (314 mg) and the mixture was stirred for 2 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate: n-hexane, 1:3, v/v) and crystallized from ethanol-water to give 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-(methoxycarbonylmethyl)quinoline (282 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate
  6. customn-hexane, 1:3, v/v) and crystallized from ethanol-water

Sources & evidence

ORD record
ord-c48af2cd19634ee0a770dabef1ac6dbb
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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