Iodine → 2-Iodo-4-methyl-6-nitroaniline

HRID 2089562Notes

Reaction equation

HRID 2089562 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[I:12]I>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[NH2:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=1[I:12]

Participants

5

Reactant 2

HCID 807IodineHCID 69784-Methyl-2-nitroaniline

Product 1

HCID 197351992-Iodo-4-methyl-6-nitroanilineYield 79.3%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

Commercially available 4-methyl-2-nitro-phenylamine (20 g, 131.5 mmol) was dissolved in ethanol (300 mL), silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with 100 mL of ethyl acetate, and concentrated. Water was added to the residue, which was then extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound (29 g, Yield 69%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through a cellite
  3. washwashed with 100 mL of ethyl acetate
  4. concentrationconcentrated
  5. additionWater was added to the residue, which
  6. extractionwas then extracted with ethyl acetate
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-c5314146acc74fe1b25d8c53d19aaf47
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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