Ammonium Chloride → 2-phenyl-1H-indol-6-amine

HRID 1896790ノート

反応式

HRID 1896790 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:13]1([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 207598016-Nitro-2-phenyl-1H-indole

生成物 1

HCID 114131282-phenyl-1H-indol-6-amine収率 35.5%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
70 °C

実験手順

6-Nitro-2-phenyl-1H-indole (175 mg, 0.73 mmol), ammonium chloride (80 mg, 1.47 mmol) and iron powder (205 mg, 3.68 mmol) were suspended in ethanol/water (4 mL/2 mL) and heated at 70° C. for 2 h. After cooling, the solution was filtrated through a pad of Celite®, which was washed with ethanol. The organic layer was evaporated into vacuo to obtain a solid, which was purified by column chromatography eluting using a gradient (ethyl acetate/hexanes 10:90 v/v to ethyl acetate/hexanes 50:50 v/v) to afford 54 mg (35%) of the title compound.

後処理

  1. temperatureAfter cooling
  2. filtrationthe solution was filtrated through a pad of Celite®, which
  3. washwas washed with ethanol
  4. customThe organic layer was evaporated into vacuo
  5. customto obtain a solid, which
  6. customwas purified by column chromatography
  7. washeluting

出典と根拠

ORDレコード
ord-42cdb75abd9d430bb0dc87cd0e385b1c
出典データセット
uspto-grants-2013_08
特許番号
US08518980B2

反応ノート

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