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

HRID 1248443

反応式

HRID 1248443 の反応式
[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]

参加物

7

反応物 3

HCID 702EthanolHCID 27483306-Fluoro-2-methyl-5-nitroquinolineHCID 178418361HCID 178418361、化合物2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 7918Acetic Anhydride溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-81cf8fc414b24f65b1cfa44e8e15e664
出典データセット
uspto-grants-1985_06
特許番号
US04524148

関連ノート

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