Stannous Chloride → 5,6-DIAMINOINDANE

HRID 1781050Notes

Reaction equation

HRID 1781050 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[CH2:7][CH2:6][CH2:5]2.Cl[Sn]Cl>C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 27636046-nitro-2,3-dihydro-1H-inden-5-amine

Product 1

HCID 106543705,6-DIAMINOINDANEYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 200 mg (1.12 mmol) of 5-amino-6-nitroindan and 1.14 g (6.01 mmol) of SnCl2 in 8 mL of ethanol was heated at 70° C. for 2 h. It was evaporated to remove the ethanol. The residue was treated with 40% aqueous NaOH to pH=12. The mixture was diluted with 4 mL of water and extracted with CHCl3 (3×10 mL). The extract was dried (MgSO4) and evaporated to leave a yellow crystalline solid (162 mg, 97%). 1H NMR (CDCl3), 2.012 (m, 2), 2.773 (t, 4, J=7.25), 3.301 (sb, 4), 6.614 (s, 2).

Workup

  1. customIt was evaporated
  2. customto remove the ethanol
  3. additionThe residue was treated with 40% aqueous NaOH to pH=12
  4. additionThe mixture was diluted with 4 mL of water
  5. extractionextracted with CHCl3 (3×10 mL)
  6. dry with materialThe extract was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-a086c150e15a42718188fdd2ed774274
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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