Acetic Acid → HCID 66756754, compound

HRID 1642598Notes

Reaction equation

HRID 1642598 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O>[Fe].CCO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66757224HCID 66757224, compound

Product 1

HCID 66756754HCID 66756754, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-benzyloxy-4-iodo-1-nitrobenzene (2.35 g, 6.62 mmol) and Fe (1.85 g, 33.1 mmol) is added AcOH (24 mL) and EtOH (12 mL) and it is refluxed at 100° C. for 1.5 h. The mixture is then cooled and filtered through Celite. EtOAc (300 mL) is added and it is then washed with saturated NaHCO3 (2×), brine (1×) and dried with NaSO4. It is then concentrated and the residue is purified by column chromatography to give the title compound.

Workup

  1. temperatureThe mixture is then cooled
  2. filtrationfiltered through Celite
  3. additionEtOAc (300 mL) is added
  4. washit is then washed with saturated NaHCO3 (2×), brine (1×)
  5. dry with materialdried with NaSO4
  6. concentrationIt is then concentrated
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-d4d18fc0be1c4f35b8cfd53a28dd7efc
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…