Methyl 4-iodo-3-nitrobenzoate → Methyl 3-amino-4-iodobenzoate

HRID 400603

Reaction equation

HRID 400603 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([NH2:11])[CH:5]=1

Participants

4

Reactant 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate

Product 1

HCID 21628210Methyl 3-amino-4-iodobenzoateYield 88.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88% yield).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of silica
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with a solution of potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d5b4f8cd506480dacb0dc38b550ddf1
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Linked notes

Loading…