Stannous Chloride → HCID 15549375, compound

HRID 1532760Notes

Reaction equation

HRID 1532760 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[N+:13]([O-])=O)[CH:2]=[CH2:3].[Sn](Cl)Cl>C(O)C>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:6]=1[NH2:13])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 15549374HCID 15549374, compound

Product 1

HCID 15549375HCID 15549375, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-allyloxy-5-cyano-2-nitrobenzene (3.6 g, 17.46 mmol) and tin (II) chloride (19.7 g, 87.3 mmol) in ethanol (100 ml) was stirred overnight at rt. The solvent was removed under reduced pressure. The reaction mixture was partitioned between 5% NaHCO3 and ethyl acetate. The mixture was filtered to remove the tin salts and the aqueous was further extracted with ethyl acetate (×4). The combined organic phases were washed with water and brine, dried over MgSO4 Removal of solvent at reduced pressure gave a brown solid (2.82 g) which was recrystallized from t-butyl-methylether/hexane to give the title compound as a pale brown solid. (2.63 g, 93%) MS(ES+) m/e 175 [M+H]+; MS(ES−) m/e 173 [M−H]−;

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe reaction mixture was partitioned between 5% NaHCO3 and ethyl acetate
  3. filtrationThe mixture was filtered
  4. customto remove the tin salts
  5. extractionthe aqueous was further extracted with ethyl acetate (×4)
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over MgSO4 Removal of solvent at reduced pressure

Sources & evidence

ORD record
ord-532db931a4db45558f7a5262131a34d2
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

Loading…