Stannous chloride dihydrate → 3-(2-Aminophenoxy)benzonitrile

HRID 558109Notes

Reaction equation

HRID 558109 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.O.O.Cl[Sn]Cl>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

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 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 SnCl2.2H2O (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-008d57ad20554caab37a853b3d439951
Source dataset
uspto-grants-2011_11
Patent number
US08063036B2

Reaction notes

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