Stannous chloride dihydrate → HCID 22349970, compound

HRID 896239Notes

Reaction equation

HRID 896239 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.O.O.Cl[Sn]Cl>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 173821411-(3,5-Dinitrophenyl)pyrrole

Product 1

HCID 22349970HCID 22349970, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3,5-dinitrophenyl)pyrrole (1.52 g, 6.52 mmol) and SnCl2.2H2O (4.4 g, 19.57 mmol) in 30 mL of ethyl acetate was stirred over weekend at RT. The solvent was removed and the residue was taken in water. The aqueous layer was basified with 1 N NaOH to dissolve the tin salts, and the product was extracted into ethyl acetate. Chromatography (silica gel, hexane:ethyl acetate, 4:1) of the crude product provided 440 mg of 1-(3-amino-5-nitrophenyl)pyrrole.

Workup

  1. customThe solvent was removed
  2. dissolutionto dissolve the tin salts
  3. extractionthe product was extracted into ethyl acetate

Sources & evidence

ORD record
ord-18e1bc5c4c884278aa72168a1ba67d0e
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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