Stannous Chloride → HCID 18365055, compound

HRID 380392Notes

Reaction equation

HRID 380392 reaction equation
[Sn](Cl)Cl.[N:4]([C:7]1[C:8]([C:14]#[N:15])=[C:9]([Cl:13])[CH:10]=[N:11][CH:12]=1)=[N+]=[N-]>C(O)C.O>[NH2:4][C:7]1[C:8]([C:14]#[N:15])=[C:9]([Cl:13])[CH:10]=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 18365076HCID 18365076, compound

Product 1

HCID 18365055HCID 18365055, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tin (II) chloride (1.42 g, 7.5 mmol) was added to a solution of 5-azido-3-chloro-4-cyanopyridine (0.9 g, 5 mmol) in ethanol (20 ml) and water (0.3 ml). Bubbling ensued. The mixture was stirred for 1 h. and then extracted twice with ethyl acetate. The extracts were washed twice with saturated aqueous sodium bicarbonate and dried over sodium sulphate. Evaporation of the solvent gave the product as an oil, which was purified by flash column chromatography on silica gel, eluting with dichloromethane/metahnol (10:1) to afford the product. MS (+CI) m/z 152 [M−H]+; 1H NMR (d6-DMSO) 8.15 (1H, s), 7.87 (1H, s), 6.88 (2H, s).

Workup

  1. customBubbling
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed twice with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulphate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-38d30329d93c456992437ed62e02619d
Source dataset
uspto-grants-2001_10
Patent number
US06303613B1

Reaction notes

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