3-(2-Nitrophenoxy)benzonitrile → 3-(2-Aminophenoxy)benzonitrile

HRID 1392059Notes

Reaction equation

HRID 1392059 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])([O-])=O>CCO>[NH2:1][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11]

Participants

3

Reactant 1

HCID 91948883-(2-Nitrophenoxy)benzonitrile

Product 1

HCID 225963353-(2-Aminophenoxy)benzonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2-nitrophenoxy)benzonitrile (1.21 g, 5 mmol, 1.0 equiv) in 30 mL of EtOH was treated with SnCl22H2O (3.38 g, 3 equiv) at reflux for 4 h. The volatile was evaporated and the residue was redissolved in EtOAc, washed with saturated aqueous NaHCO3 and 1N NaOH. The organic layer was dried over MgSO4, filtered and evaporated to give 3-(2-aminophenoxy)benzonitrile (1.04 g, 99%). MS found for C13H11N2O (M+H)+: 211.

Workup

  1. temperatureat reflux for 4 h
  2. customThe volatile was evaporated
  3. dissolutionthe residue was redissolved in EtOAc
  4. washwashed with saturated aqueous NaHCO3 and 1N NaOH
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-247c7f12546a44e5840e7efefe446a73
Source dataset
uspto-grants-2008_03
Patent number
US07342013B2

Reaction notes

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