Ammonium Chloride → (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline

HRID 1255851노트

반응식

HRID 1255851 반응식
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH3:10])[N:3]=1.[Cl-].[NH4+].[In]>C(O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([O:8][C@@H:9]([C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[NH2:17])[CH3:10])[CH:5]=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 86641862(R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine

생성물 1

HCID 86641863(R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline수율 74.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of (R)-2-chloro-6-(1-(3-nitrophenyl)ethoxy)pyrazine (240 mg, 0.86 mmol) in ethanol (12 mL) was added a solution of ammonium chloride (460 mg, 8.6 mmol) in water (6 mL), then indium powder (394 mg, mesh 100, 3.4 mmol). The mixture was heated at reflux for 20 hours, was allowed to cool to room temperature and was filtered through Celite. The filter cake was washed with ethanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and was washed with water (15 mL), brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline as a dark yellow liquid (160 mg).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. filtrationwas filtered through Celite
  4. washThe filter cake was washed with ethanol
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  7. washwas washed with water (15 mL), brine (15 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6a56103e5dda46caa51ac04d97ab950d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461161B2

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