Potassium Carbonate → HCID 19592775, compound

HRID 613484Notes

Reaction equation

HRID 613484 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH3:17])=[CH:12]2)=[O:5].BrN1[C:28](=[O:29])[CH2:27]CC1=O.N(C(C)(CC(C)(OC)C)C#N)=NC(C)(CC([O:40]C)(C)C)C#N.BrCC1C=NC2C(C=1)=CC=CC=2NC(=O)C1C(Cl)=CC=CC=1Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C)C=O.O.C(O)(=O)C>[C:28]([O:29][CH2:17][C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:4](=[O:5])[C:3]1[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:2]=1[Cl:1])(=[O:40])[CH3:27]

Participants

12

Reactant 5

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 195923883-Bromomethyl-8-(2,6-dichlorobenzoylamino)quinolineHCID 195927078-(2,6-Dichlorobenzoylamino)-3-methylquinoline

Product 1

HCID 19592775HCID 19592775, compoundYield 379.7%

Reagents, catalysts & solvents 6

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-3-methylquinoline (108 mg), N-bromosuccinimide (69.6 mg) and 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) (10.1 mg) in dichloromethane and carbon tetrachloride was refluxed for 2 hours. After cooling, the mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 3-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline. The residue was dissolved in dimethylformamide, and acetic acid (27.5 mg) and potassium carbonate (63.2 mg) were added thereto. After stirring for 3 hours at ambient temperature, the mixture was poured into water and extracted with ethyl acetate. 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-dichloromethane) to give 3-acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (48.4 mg).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. washwashed with water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customto give a residue
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-725aa1605c534dd2b48cacc246144f71
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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