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

HRID 842851Notes

Reaction equation

HRID 842851 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 SnCl2H2O (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-f7d8146bb7124ee79b84faef4ab93b6f
Source dataset
uspto-grants-2002_04
Patent number
US06376515B2

Reaction notes

Loading…