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

HRID 727120

반응식

HRID 727120 반응식
[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]

참가 물질

5

반응물 2

HCID 24502Potassium Dichromate2회HCID 10805264HCID 10805264, 화합물

생성물 1

HCID 98345267-Acetamido-2-methylquinoline-5,8-dione수율 56%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-7df47707b06d4b5abc3d13e98ede7682
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712289

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