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Potassium Dichromate → 7-Acetamido-2-methylquinoline-5,8-dione

HRID 1760197
ノート
印刷プレビュー

反応式

HRID 1760197 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 24502Potassium Dichromate2 回HCID 108052645,7-Diacetamido-2-methyl-8-acetoxyquinoline

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-dd53a72979104252bc6d414557411f9d
出典データセット
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06841555B2

反応ノート

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