Ammonium Chloride → (R)-3-(1-(6-chloropyrazin-2-yloxy)ethyl)aniline
Reaction equation
[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]=1Participants
6
Procedure
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).
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 20 hours
- filtrationwas filtered through Celite
- washThe filter cake was washed with ethanol
- concentrationthe combined filtrates were concentrated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate (25 mL)
- washwas washed with water (15 mL), brine (15 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6a56103e5dda46caa51ac04d97ab950d
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461161B2
Reaction notes
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