Hydrogen Peroxide → 2-Amino-5-iodobenzonitrile

HRID 1026620Notes

Reaction equation

HRID 1026620 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[I-:10].[NH4+].OO.ClCCl>C(O)(=O)C.CCCCCC>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 25487Ammonium iodideHCID 729132-Aminobenzonitrile

Product 1

HCID 99648032-Amino-5-iodobenzonitrileYield 48.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8058HexaneSolvent

Procedure

2-Amino-benzonitrile (10 g, 0.085 mol) and ammonium iodide (13.5 g, 0.094 mol) were dissolved in acetic acid (200 mL). 30% aqueous hydrogen peroxide solution (5.3 mL, 0.094 mL) was slowly added at room temperature and stirred for 12 h. After completion of the reaction, the reaction solution was filtered through celite. The filtrate was treated with aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. The solid obtained using dichloromethane (10 mL) and hexane (200 mL) was filtered and dried under nitrogen gas to give the title compound (10 g, Yield 48%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered through celite
  3. additionThe filtrate was treated with aqueous sodium thiosulfate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe solid obtained
  8. filtrationwas filtered
  9. customdried under nitrogen gas

Sources & evidence

ORD record
ord-7a9d20201e8c4033869cc1b5e24cd776
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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