Stannous Chloride → HCID 15549375, compound

HRID 1067751Notes

Reaction equation

HRID 1067751 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:8]#[N:9])[CH:2]=[CH2:3].[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C(O)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:8]#[N:9])[CH:10]=[CH:11][C:12]=1[NH2:13])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 15549374HCID 15549374, compound

Product 1

HCID 15549375HCID 15549375, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 3-allyloxy-4-nitrobenzonitrile (5.85 g, 28.68 mmol) in ethanol (30 ml), Tin (II) chloride (32 g, 143.4 mmol) was added. The reaction mixture was stirred at reflux for 4 hours and then was cooled to room temperature. NaHCO3 (aq) was added to pH=7 was achieved. Then the reaction mixture was extracted with ethyl acetate (3×). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (4.5 g, 90%). EI-MS m/z 175 (M+).

Workup

  1. temperatureat reflux for 4 hours
  2. extractionThen the reaction mixture was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96a1eb2814bf478d93f055ca69efc804
Source dataset
uspto-grants-2001_06
Patent number
US06248785B1

Reaction notes

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