重铬酸钾 → 7-Acetamido-2-methylquinoline-5,8-dione

HRID 263934

反应方程式

HRID 263934 反应方程式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[K+].[K+].C(N[C:16]1[CH:25]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[C:23]([O:30]C(=O)C)=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH3:34])=[N:21]2)(=O)C>C(O)(=O)C.O>[C:27]([NH:26][C:24]1[C:23](=[O:30])[C:22]2[N:21]=[C:20]([CH3:34])[CH:19]=[CH:18][C:17]=2[C:16](=[O:2])[CH:25]=1)(=[O:29])[CH3:28]

参与物

5

反应物 2

HCID 24502重铬酸钾2 次HCID 10805264HCID 10805264，化合物

产物 1

HCID 98345267-Acetamido-2-methylquinoline-5,8-dione收率 56%

试剂、催化剂与溶剂 2

HCID 176醋酸溶剂2 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次

实验过程

This compound was prepared by the oxidation of the corresponding acylamido with potassium dichromate in glacial acetic acid. Into a 1000 ml Erlenmeyer flask, 240 ml of glacial acetic acid, and 5,7-diacetamido-2-methyl-8-acetoxyquinoline (31) (prepared as described in Example 31) (6.3 g, 2.0 mmol) were added. To the resulting suspension, a solution of potassium dichromate (17.64 g) in 200 ml of water was added. This black solution was magnetically stirred at room temperature for 20-24 hours. The solution was then poured into 900 ml of water and extracted with dichloromethane (5×200 ml). The organic extracts were washed with a solution of 5% sodium carbonate in a saturated salt solution (3×300 ml). The organic layer was dried overnight with anhydrous magnesium sulfate. The magnesium sulfate was filtered off, and the solvent was evaporated to leave an orange/yellow solid. The solid 7-acetamino-2-methylquinoline-5,8-dione (27) was dried overnight under vacuum. 2.6 g of product was obtained for a yield of 56%.

后处理

  1. extractionextracted with dichloromethane (5×200 ml)
  2. washThe organic extracts were washed with a solution of 5% sodium carbonate in a saturated salt solution (3×300 ml)
  3. dry with materialThe organic layer was dried overnight with anhydrous magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe solvent was evaporated
  6. customto leave an orange/yellow solid
  7. dry with materialThe solid 7-acetamino-2-methylquinoline-5,8-dione (27) was dried overnight under vacuum

来源与证据

ORD记录
ord-78ffd28c4f884ec0a5e810fc1ef12593
来源数据集
uspto-grants-1997_07
专利号
US05646150

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