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

HRID 572207Notes

Reaction equation

HRID 572207 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2943542f228746ac918d7e9fcb6cb2db
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Reaction notes

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