Methyl iodide → HCID 19592958, compound

HRID 613548Notes

Reaction equation

HRID 613548 reaction equation
[C:1]([N:4]([CH3:27])[NH:5][C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:17](=[O:26])[C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[CH3:28]C(C)([O-])C.[K+].CI>CN1CCCC1=O.C(OCC)(=O)C>[C:1]([N:4]([CH3:27])[N:5]([C:6]1[C:15]2[C:10](=[C:11]([NH:16][C:17](=[O:26])[C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][CH:7]=1)[CH3:28])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 19592886HCID 19592886, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19592958HCID 19592958, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-(2-acetyl-2-methylhydrazino)-8-(2,6-dichlorobenzoylamino)quinoline (140 mg) in N-methylpyrrolidone (1.5 ml) was added potassium tert-butoxide (40.9 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. Methyl iodide (59.1 mg) was added thereto under ice-cooling, and the mixture was stirred for 12 hours at ambient temperature. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (methanol-dichloromethane) and recrystallized from ethanol to give 4-(2-acetyl-1,2-dimethylhydrazino)-8-(2,6-dichlorobenzoylamino)quinoline (62 mg).

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred for 12 hours at ambient temperature
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography (methanol-dichloromethane)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6655ecee68774f60b84b8ae0cd2de29b
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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