Ethanol → N-(6-Fluoro-2-methylquinolin-5-yl)acetamide

HRID 637436

반응식

HRID 637436 반응식
[F:1][C:2]1[C:3]([N+:13]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[H][H].[CH2:18]([OH:20])[CH3:19]>C(OCC)(=O)C.C(OC(=O)C)(=O)C.[Pd]>[C:18]([NH:13][C:3]1[C:2]([F:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH3:12])=[N:8]2)(=[O:20])[CH3:19]

참가 물질

7

반응물 3

HCID 702EthanolHCID 27483306-Fluoro-2-methyl-5-nitroquinolineHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 12896814N-(6-Fluoro-2-methylquinolin-5-yl)acetamide

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 7918Acetic Anhydride용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 20 g (0.1 mole) of 6-fluoro-5-nitroquinaldine in 180 ml of ethyl acetate and 20 ml of acetic anhydride were added 3 g of ten percent palladium on charcoal. The mixture was hydrogenated with hydrogen gas at 50 psi on a Paar apparatus for 20 minutes. The theoretical amount of hydrogen (25 psi) was used. On cooling, the mixture solidified to a yellow mass. About 200 ml of ethanol was added, and the mixture was heated to dissolve the product. The catalyst was filtered off through celite, and the filtrate was evaporated to dryness, leaving a yellow solid. This solid was triturated with 200 ml of water and neutralized with ten percent sodium hydroxide solution. Filtration and drying provided white crystals of 5-acetamido-6-fluoroquinaldine, m.p. 232°-235° C. The structural assignment was confirmed by infrared spectral analysis.

후처리

  1. temperatureOn cooling
  2. temperaturethe mixture was heated
  3. dissolutionto dissolve the product
  4. filtrationThe catalyst was filtered off through celite
  5. customthe filtrate was evaporated to dryness
  6. customleaving a yellow solid
  7. customThis solid was triturated with 200 ml of water and neutralized with ten percent sodium hydroxide solution
  8. filtrationFiltration
  9. customdrying

출처 및 근거

ORD 기록
ord-86a3fff339764410ae18d2e9da40aa9a
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04556713

연결된 노트

불러오는 중…