Ethanol → (2-Amino-3-chlorophenyl)amine
Reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CCO.[Cl-].[NH4+]>[Zn].O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([NH2:5])[C:3]=1[NH2:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of 3-chloro-2-nitroaniline (684 mg) and EtOH (5 mL) were added ammonium chloride (353 mg) and water (1.5 mL), followed by adding zinc powder (1.38 g) at 80° C., and heating and stirring at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, filtered over Celite, and washed with EtOAc. This filtrate was washed with a saturated aqueous NaHCO3 solution and brine in this order, dried over MgSO4, and then concentrated under reduced pressure to obtain 3-chlorobenzene-1,2-diamine.
Workup
- temperatureheating
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered over Celite
- washwashed with EtOAc
- washThis filtrate was washed with a saturated aqueous NaHCO3 solution and brine in this order
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8b8d6cb8fb2149a0aac516a7f34719ac
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937087B2
Reaction notes
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