Ammonium Chloride → N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine

HRID 1255829ノート

反応式

HRID 1255829 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH3:10])[CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].[In]>C(O)C.O>[NH2:17][C:13]1[CH:12]=[C:11]([C@@H:9]([NH:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[CH3:10])[CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 866418566-bromo-N-[(1S)-1-(3-nitrophenyl)ethyl]pyridin-2-amine

生成物 1

HCID 86641857N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine収率 77.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 6-bromo-N-[(1S)-1-(3-nitrophenyl)ethyl]pyridin-2-amine (100 mg, 0.31 mmol) in ethanol (5 mL) was added a solution of ammonium chloride (166 mg, 3.1 mmol) in water (2.5 mL), then indium powder (142 mg, mesh 100, 1.24 mmol). The mixture was heated at reflux for 4.5 hours, was allowed to cool to room temperature and was filtered through Celite. The filter cake was washed with water and ethanol and the combined filtrates were extracted with dichloromethane (2×30 mL) and the extracts washed with brine (30 mL), dried (Na2SO4) and concentrated under reduced pressure to give N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine (70 mg, 77%) as a dark yellow oil.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4.5 hours
  3. filtrationwas filtered through Celite
  4. washThe filter cake was washed with water and ethanol
  5. extractionthe combined filtrates were extracted with dichloromethane (2×30 mL)
  6. washthe extracts washed with brine (30 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6fd67f33b2c94ed4a2a2ac85edb7d796
出典データセット
uspto-grants-2013_06
特許番号
US08461161B2

反応ノート

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