m-Chloroperbenzoic acid → 1-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 375902ノート

反応式

HRID 375902 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:24].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17]([CH3:18])=[O:24])=[CH:11][CH:10]=3)[CH3:2]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 212177171-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

生成物 1

HCID 212176981-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline収率 93.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3, 4-b]quinoline (2.4 g, 8.7 mmol) in CHCl3 (50 mL) at -40° C. was added m-chloroperoxybenzoic acid (2.75 g, 8.7 mmol). The reaction mixture was slowly warmed to 0° C. and then saturated NaHCO3 (10 mL) was added. The reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL), the layers were separated and then the aqueous layer was extracted with CH2Cl2 (20 ml). The CH2Cl2 extracts were combined, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 50% ether/hexane, then 25% ethyl acetate/25% hexane/50% ether and finally ethyl acetate (100%) to afford 2.4 g of 1-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline.

後処理

  1. customThe reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL)
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 50% ether/hexane

出典と根拠

ORDレコード
ord-3e232b56fa0a4bb5a6b18888c6a443b8
出典データセット
uspto-grants-1996_01
特許番号
US05488055

反応ノート

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