HCID 11279266, compound → HCID 43479596, compound

HRID 2355378Notes

Reaction equation

HRID 2355378 reaction equation
[I:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>C(O)C.O>[I:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

4

Reactant 1

HCID 11279266HCID 11279266, compound

Product 1

HCID 43479596HCID 43479596, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(2-iodophenoxy)-2-nitrobenzene (9.60 g, 28.1 mmol) and SnCl.2H2O (13.0 g, 56.0 mmol) in ethanol (25 mL) and water (5 mL) was refluxed until no starting material remained (˜1 h). The ethanol was removed in vacuo and the aq layer was basified to pH>10 and extracted with CH2Cl2 (4×10 mL). The combined organic layers were dried over Na2SO4, and the solvent was removed to give a crude 2-(2-Iodophenoxy)benzenamine (8.57 g, 98%), which was used for the next step without purification.

Workup

  1. custom(˜1 h)
  2. customThe ethanol was removed in vacuo
  3. extractionextracted with CH2Cl2 (4×10 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-16ac2f2f664b42fb880c4e7e0affc6f3
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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