Ammonium Chloride → 2-Chloro-5-iodoaniline
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[Cl-].[NH4+]>CO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[NH2:9]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
To 1-chloro-4-iodo-2-nitrobenzene (1.27 g, 4.49 mmol) in methanol (20 ml) was added iron powder (1.25 g, 22 mmol) and the reaction heated to 50° C. A solution of ammonium chloride (1.92 g, 36 mmol) in water (10 ml) was added slowly and the reaction heated to 70° C. overnight. Reaction was cooled, filtered through celite, washed with methanol and solvent reduced in vacuo. The residue was purified by chromatography on silica gel (gradient of hexane to 10% ethyl acetate in hexane) to afford the title compound. MS (ES+) m/e 254 [M+H]+.
Workup
- temperaturethe reaction heated to 70° C. overnight
- customReaction
- temperaturewas cooled
- filtrationfiltered through celite
- washwashed with methanol and solvent
- customThe residue was purified by chromatography on silica gel (gradient of hexane to 10% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-53c183b689d5480f9542ee56d403ca19
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381728B2
Reaction notes
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