Ethanol → 3-(1-Amino-2-naphthoyl)benzonitrile

HRID 1191304ノート

反応式

HRID 1191304 の反応式
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=[O:15])([O-])=O.C(O)C.O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=[O:15]

参加物

6

反応物 3

HCID 702EthanolHCID 962WaterHCID 866904463-(1-Nitro-2-naphthoyl)benzonitrile

生成物 1

HCID 866904473-(1-Amino-2-naphthoyl)benzonitrile収率 96.3%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

3-(1-nitro-2-naphthoyl)benzonitrile (6.22 g, 20.6 mmol) was dissolved at 65° C. in acetic acid (150 mL), ethanol (150 mL) and water (15 mL). After cooled to room temperature, to the solution was added iron powder (6.67 g, 119 mmol). To the mixture was stirred at 65° C. for 1 hour, and cooled to room temperature. The resultant mixture was added silica gel (100 g), filtered, and the residue was washed with ethyl acetate. The filtrate and washings were combined, washed with a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform), to give the titled compound as a yellow crystal (5.40 g, yield 96%).

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washthe residue was washed with ethyl acetate
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform)

出典と根拠

ORDレコード
ord-f195748a06654646acb3b4883869c4b5
出典データセット
uspto-grants-2014_03
特許番号
US08680110B2

反応ノート

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