Iodide Ion → 6-iodo-2,3-dihydro-1H-inden-5-amine

HRID 537974Notes

Reaction equation

HRID 537974 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[I-:11]>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 30165Iodide IonHCID 90496Indan-5-amine

Product 1

HCID 224002936-iodo-2,3-dihydro-1H-inden-5-amineYield 43.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-aminoindan (423 mg, 3.17 mmol), silver sulfate (990 mg, 3.17 mmol) and iodide (805 mg, 3.17 mmol) in methanol (20 mL) was stirred at room temperature overnight. The mixture was filtered and the solid was washed with a small amount of methanol. The filtrate was quenched with saturated Na2S2O3 and then diluted with water. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried (Na2SO4) and concentrated in vacuo. Flash chromatography (Si, hexanes/EtOAc) of the residue yielded 6-iodoindan-5-amine (354 mg, 43%). LCMS calc.=258.99; found=260.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.51 (s, 1H), 6.69 (s, 1H), 3.97 (br, s, 2H), 3.02-2.90 (m, 1H), 2.81 (d, J=7.1 Hz, 3H), 2.12-2.02 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with a small amount of methanol
  3. customThe filtrate was quenched with saturated Na2S2O3
  4. additiondiluted with water
  5. extractionThe aqueous layer was extracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine (1×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d9b0afdba204b15a7016359ae4f6497
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

Loading…