Sodium Hydroxide → 1-Chloro-3-(4-aminophenoxy)propane
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[OH-].[Na+]>CCO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-chloro-3-(4-nitrophenoxy)propane (830 mg, 3.85 mmol), stannous chloride dihydrate (4.3 g, 19.25 mmol), and EtOH (20 mL) was heated under reflux for 3 hours. The mixture was cooled, 2.5N NaOH (19 mL) was added, and the precipitate was removed by filtration. The filtrate was concentrated to 10 mL and extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 700 mg (98%) of product as a brown oil.
Workup
- temperaturewas heated
- temperatureunder reflux for 3 hours
- temperatureThe mixture was cooled
- customthe precipitate was removed by filtration
- concentrationThe filtrate was concentrated to 10 mL
- extractionextracted with EtOAc
- dry with materialThe extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a4a9a3e2a9ec4d1cbadba9c6902fe7d1
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05104892
Reaction notes
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