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

HRID 1255829Notes

Reaction equation

HRID 1255829 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-6fd67f33b2c94ed4a2a2ac85edb7d796
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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