Acetic Acid → HCID 66756754, compound

HRID 660473Notes

Reaction equation

HRID 660473 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 sat. 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 sat. 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-30cfb3fb1f614f6fb40135e35e666de7
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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