Ethanol → N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine

HRID 387991ノート

反応式

HRID 387991 の反応式
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(O)C.O>C(OCC)(=O)C.CCCCCC.[Fe]>[NH2:1][C:4]1[CH:23]=[CH:22][C:7]([O:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 22936302N-(6-(4-Nitrophenoxy)pyrimidin-4-yl)phenylamine

生成物 1

HCID 22936405N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine収率 84.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

After suspending N-(6-(4-nitrophenoxy)pyrimidin-4-yl)phenylamine (508 mg, 1.65 mmol), iron powder (461 mg, 8.25 mmol) and ammonium chloride (882 mg, 16.5 mmol) in an ethanol (16 ml)-water (4 ml) mixed solvent, the suspension was heated and stirred at 80° C. for 20 minutes. Upon completion of the reaction, the reaction mixture was filtered with celite and washed in ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (387 mg, 1.39 mmol, 84%) as colorless crystals.

後処理

  1. additionmixed solvent
  2. temperaturethe suspension was heated
  3. customUpon completion of the reaction
  4. filtrationthe reaction mixture was filtered with celite
  5. washwashed in ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationthe drying agent was filtered off
  9. distillationthe filtrate was distilled off under reduced pressure
  10. customThe obtained crude product
  11. filtrationthe crystals were filtered out
  12. washwashed with hexane
  13. customblow-dried

出典と根拠

ORDレコード
ord-eba07ec767f844c5b7caa91a109ab291
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

反応ノート

読み込み中…