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

HRID 604609노트

반응식

HRID 604609 반응식
[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]

참가 물질

5

반응물 2

HCID 30165Iodide IonHCID 90496Indan-5-amine

생성물 1

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

시약·촉매·용매 2

HCID 178418844HCID 178418844, 화합물촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-136a2d2a1a8645b680e7a34a2069da15
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

반응 노트

불러오는 중…