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

HRID 604609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604609
[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]

Komponenten

5

Edukt 2

HCID 30165Iodide IonHCID 90496Indan-5-amine

Produkt 1

HCID 224002936-iodo-2,3-dihydro-1H-inden-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418844HCID 178418844, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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 CH3OH (20 mL) was stirred at room temperature overnight. The mixture was filtered and the solid was washed with a small amount of CH3OH. 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 afforded 6-iodoindan-5-amine. LCMS calc.=260.0; 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).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with a small amount of CH3OH
  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

Quellen und Nachweise

ORD-Eintrag
ord-136a2d2a1a8645b680e7a34a2069da15
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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