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

HRID 1586186ノート

反応式

HRID 1586186 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. is added m-chloroperoxybenzoic acid (2.75 g, 8.7 mmol). The reaction mixture is slowly warmed to 0° C. and then saturated NaHCO3 (10 ml) is added. The reaction mixture is partitioned between water (20 ml) and CH2Cl2 (20 ml), the layers are separated and then the aqueous layer is extracted with CH2Cl2 (20 ml). The CH2Cl2 extracts are combined, dried over MgSO4 and evaporated. The residue is 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 is partitioned between water (20 ml) and CH2Cl2 (20 ml)
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with CH2Cl2 (20 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue is purified by column chromatography on silica gel eluting with 50% ether/hexane

出典と根拠

ORDレコード
ord-98eddf10ab54442bbb3585dbeec25967
出典データセット
uspto-grants-1999_08
特許番号
US05942520

反応ノート

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