Hydrogen Peroxide → 6-Chloro-7-methoxyquinoline 1-oxide

HRID 579333ノート

反応式

HRID 579333 の反応式
[OH:1]O.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[CH:7]2>C(Cl)Cl.O=[Mn]=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N+:10]([O-:1])=[CH:9][CH:8]=[CH:7]2

参加物

5

反応物 2

HCID 784Hydrogen PeroxideHCID 867271546-Chloro-7-methoxyquinoline

生成物 1

HCID 867271566-Chloro-7-methoxyquinoline 1-oxide

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 6344Dichloromethane溶媒

実験手順

In a 100 mL round bottom flask, 6-chloro-7-methoxyquinoline was dissolved in DCM (25.8 mL) and MTO (0.051 g, 0.207 mmol) was added. The reaction mixture was capped and vented with a needle, then placed in an ice bath to cool. Once cool, hydrogen peroxide (0.633 mL, 10.33 mmol) was added drop-wise. When the addition was complete, the reaction mixture was removed from cooling, warmed to room temperature and stirred overnight (18 h). MnO2 (10 mg, 0.115 mmol) was added and the reaction mixture was stirred for an additional 2 h. The reaction mixture was filtered through celite, washing with DCM, then concentrated in vacuo to yield 6-chloro-7-methyoxyquinoline 1-oxide (1.036 g) MS [M+H+]=210.3.

後処理

  1. additionMTO (0.051 g, 0.207 mmol) was added
  2. customThe reaction mixture was capped
  3. customplaced in an ice bath
  4. temperatureto cool
  5. temperatureOnce cool
  6. additionWhen the addition
  7. customthe reaction mixture was removed
  8. temperaturefrom cooling
  9. stirringthe reaction mixture was stirred for an additional 2 h
  10. filtrationThe reaction mixture was filtered through celite
  11. washwashing with DCM
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-08b1e63a24ed4945a959e4fa26f63dac
出典データセット
uspto-grants-2015_05
特許番号
US09040712B2

反応ノート

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