4-Nitroaniline → 2-Iodo-4-nitroaniline

HRID 1769633Notes

Reaction equation

HRID 1769633 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[I:11]Cl.C(OCC)(=O)C>C(#N)C>[I:11][C:9]1[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 8857Ethyl AcetateHCID 24640Iodine chloride

Product 1

HCID 2226292-Iodo-4-nitroanilineYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-nitroaniline (27.6 g, 0.2 mol) in 200 mL of dry acetonitrile was added a solution of ICl (31.0 g, 0.19 mol) in 50 mL of acetonitrile and the mixture was stirred at room temperature for 18 h. The reaction mixture was then poured into ethyl acetate, washed (20% aq. Na2S2O3, brine), dried (Na2SO4) and evaporated to give a brown solid. Chromatography (SiO2 /CH2Cl2 -hexane, 6:4 to 7:3) afforded the title compound (18.0 g, 36%) as a yellow solid, mp 104°-106° C.: IR (neat) 3480, 3380, 1610, 1300 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ8.38 (d, J=2.6 Hz, 1H), 7.97 (dd, J=9.0, 2.6 Hz, 1H), 6.75 (d, J=9.0 Hz, 1H), 6.73 (s, 2H).

Workup

  1. washwashed (20% aq. Na2S2O3, brine)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give a brown solid

Sources & evidence

ORD record
ord-3bb0f858b6404a45abd9676f4cdde444
Source dataset
uspto-grants-1995_01
Patent number
US05382592

Reaction notes

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