Stannous Chloride → 9H-carbazole-2,7-diamine

HRID 2307948Notes

Reaction equation

HRID 2307948 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([N+:17]([O-])=O)=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)([O-])=O.[Sn](Cl)Cl>C(O)(=O)C.Cl>[NH2:1][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([NH2:17])=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 13266881HCID 13266881, compound

Product 1

HCID 43918679H-carbazole-2,7-diamineYield 78.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of compound 3 (6.00 g, 23.3 mmol) in a mixture of acetic acid (200 mL) and hydrochloric acid (35 mL) was added 44.3 g (0.024 mol, Aldrich Co.) of tin(II) chloride. The mixture was refluxed for 24 h under argon. After cooling, the precipitate was separated from the solvent by filtration and washed several times with cold acetic acid. The resulting diammonium salt was dissolved in water followed by addition of an aqueous solution of sodium hydroxide until the pH was around 10. The precipitate was collect by filtration and dried under vacuum. Recristallization in ethanol afforded 3.60 g of the title product as a shiny gray solid. M.P. 248° C. (dec.). (Yield: 78%).

Workup

  1. temperatureThe mixture was refluxed for 24 h under argon
  2. temperatureAfter cooling
  3. customthe precipitate was separated from the solvent by filtration
  4. washwashed several times with cold acetic acid
  5. dissolutionThe resulting diammonium salt was dissolved in water
  6. additionfollowed by addition of an aqueous solution of sodium hydroxide until the pH was around 10
  7. filtrationThe precipitate was collect by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-df6dceba53c0453da03a900ffff1dede
Source dataset
uspto-grants-2004_12
Patent number
US06833432B2

Reaction notes

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