4-Iodo-2-nitrotoluene → 5-Iodo-o-toluidine

HRID 2373348Notes

Reaction equation

HRID 2373348 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pt]>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([NH2:9])[CH:3]=1

Participants

5

Reactant 2

HCID 1704814-Iodo-2-nitrotolueneHCID 2723923Ammonium formate

Product 1

HCID 5228025-Iodo-o-toluidine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-iodo-1-methyl-2-nitro-benzene (25.0 g, 107 mmol) in 300 mL of ethanol was added sulfided platinum (3.00 g) and ammonium formate (20.3 g, 321 mmol). The mixture was heated to reflux for 12 h and then cooled to 22° C., filtered through Celite® and concentrated in vacuo. The resulting residue was diluted with H2O (300 mL) and extracted with 3×200 mL CH2Cl2. The organic fractions were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give b (21.1 g, 95%): MS m/z═234 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationfiltered through Celite®
  4. concentrationconcentrated in vacuo
  5. additionThe resulting residue was diluted with H2O (300 mL)
  6. extractionextracted with 3×200 mL CH2Cl2
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto give b (21.1 g, 95%)

Sources & evidence

ORD record
ord-53b10a9785974322b88cc8018bbcabbe
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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