Iodine → 2-Iodo-4-nitroaniline

HRID 2378438Notes

Reaction equation

HRID 2378438 reaction equation
[I:1]I.[N+:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)([O-:5])=[O:4]>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:11]1[CH:12]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

5

Reactant 2

HCID 807IodineHCID 74754-Nitroaniline

Product 1

HCID 2226292-Iodo-4-nitroaniline

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a mixture of iodine (46.0 g, 0.180 mol) and silver sulfate (56.3 g, 0.180 mol) in anhydrous ethanol (500 mL) was added 4-nitroaniline (25.0 g, 0.180 mol) and the reaction mixture was stirred for 5 h at rt. The resulting yellow solution was filtered and concentrated in vacuo. The resulting residue was dissolved into 400 mL ethyl acetate, washed with 1N sodium hydroxide solution (2×250 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to yield 45.5 (95%) of compound 489A, as a yellow solid. HPLC: 98% at 2.837 min (retention time) (Shimadzu VP-ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.1% trifluoracetic acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 265.08 [M+H]+.

Workup

  1. filtrationThe resulting yellow solution was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue was dissolved into 400 mL ethyl acetate
  4. washwashed with 1N sodium hydroxide solution (2×250 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c322fcb2f8b340a787c8c1220b4b73f1
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

Loading…