2-Aminobenzonitrile → 2-Amino-5-iodobenzonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[I:10]N1C(=O)CCC1=O.C1C(=O)N(I)C(=O)C1.CN(C=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Aminobenzonitrile (2.0 g, 16.9 mmol, 1 equiv.) was dissolved in dry N,N-dimethylformamide (30 mL), and the solution was cooled to 0° C. A solution of N-iodosuccinimide, NIS (3.81 g, 16.9 mmol, 1 equiv.) in 30 mL of DMF was added dropwise with an addition funnel. After the NIS/DMF solution was, added, the ice bath was removed, and the reaction was stirred at room temperature overnight. The reaction was quenched by pouring into 3N NaOH (300 mL) and diluted with an additional 200 mL of water. 2-Amino-5-iodobenzonitrile formed as a precipitate, which was collected by filtration.
Workup
- additionadded
- customthe ice bath was removed
- customThe reaction was quenched
- additionby pouring into 3N NaOH (300 mL)
- additiondiluted with an additional 200 mL of water
Sources & evidence
- ORD record
- ord-1ab1fd58faad45c186e551e793b6ee7d
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217794B2
Reaction notes
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