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

HRID 537974노트

반응식

HRID 537974 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-amine수율 43.1%

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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-7d9b0afdba204b15a7016359ae4f6497
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865707B2

반응 노트

불러오는 중…