Potassium Carbonate → HCID 19592775、化合物

HRID 613484

反応式

HRID 613484 の反応式
[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]

参加物

12

反応物 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

生成物 1

HCID 19592775HCID 19592775、化合物収率 379.7%

試薬・触媒・溶媒 6

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-725aa1605c534dd2b48cacc246144f71
出典データセット
uspto-grants-1999_12
特許番号
US06008230

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