Iodine → 2-Iodo-4,6-dinitroaniline

HRID 2299160Notes

Reaction equation

HRID 2299160 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[I:14]I.C(Cl)(Cl)Cl>CC(O)=O.CCOC(C)=O.[Hg](OC(C)=O)OC(C)=O>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([I:14])[C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 807IodineHCID 6212ChloroformHCID 73212,4-Dinitroaniline

Product 1

HCID 183798712-Iodo-4,6-dinitroanilineYield 81.3%

Reagents, catalysts & solvents 3

HCID 16683746DiacetyloxymercuryCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dinitroaniline (3.0 g, 16 mmol) and Hg(OAc)2 (6.8 g, 21 mmol) in 40 ml of AcOH was added 5.0 g (19 mmol) of I2 in 100 ml of AcOH dropwise and reaction mixture was stirred for 12 h. The reaction mixture was concentrated in vacuo, yielding a dark residue which was diluted with EtOAc and washed with aqueous NaHCO3. Organic layer was dried over MgSO4 and concentrated in vacuo to produce dark residue which was subjected to column chromatography (CHCl3, neat) to provide 4.1 g (13 mmol, 81%) of 2,4-dinitro-6-iodoaniline.

Workup

  1. customreaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customyielding a dark residue which
  4. washwashed with aqueous NaHCO3
  5. dry with materialOrganic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto produce dark residue which

Sources & evidence

ORD record
ord-cbe75744bbc34e508378839d5272e7c4
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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