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

HRID 1255829노트

반응식

HRID 1255829 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6fd67f33b2c94ed4a2a2ac85edb7d796
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461161B2

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