Ammonium Chloride → (S)-1-(2-Bromophenyl)ethanamine

HRID 605338Notes

Reaction equation

HRID 605338 reaction equation
[N:1]([C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Br:12])[CH3:5])=[N+]=[N-].[NH4+].[Cl-].[In]>CCO.O>[Br:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C@@H:4]([NH2:1])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 866155641-[(1S)-1-azidoethyl]-2-bromobenzene

Product 1

HCID 2530257(S)-1-(2-Bromophenyl)ethanamineYield 88%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of (S)-1-(1-azidoethyl)-2-bromobenzene (45 mg, 0.2 mmol) in EtOH/H2O (5 mL/5 mL) was added in NH4Cl (108 mg, 2.0 mmol) and indium (91 mg, 0.8 mmol). The mixture was refluxed overnight. The reaction mixture was filtered, washed with EtOH and evaporated. The residue was triturated with AcOEt and filtered. The filtrate was evaporated to give the title compound (35 mg, 88%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtOH
  4. customevaporated
  5. customThe residue was triturated with AcOEt
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-041214f9c7a8431296a83e4f76dac554
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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