Isoamyl Nitrite → 6-Iodoindane-5-carbonitrile

HRID 604611노트

반응식

HRID 604611 반응식
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]#[N:12].N(OCCC(C)C)=O.[I-:21]>C(Cl)(Cl)Cl>[I:21][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]#[N:12]

참가 물질

5

반응물 3

HCID 8053Isoamyl NitriteHCID 30165Iodide IonHCID 451221766-amino-2,3-dihydro-1H-indene-5-carbonitrile

생성물 1

HCID 575762696-Iodoindane-5-carbonitrile

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 6-aminoindane-5-carbonitrile (48.5 mg, 0.307 mmol), isoamyl nitrite (82 μL, 0.614 mmol) and iodide (85.7 mg, 0.338 mmol) in dry CHCl3 (2 mL) was stirred at room temperature for 0.5 h. The mixture was then heated at 80° C. under N2 for 2 h. The reaction mixture was quenched with saturated Na2S2O3 and partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 6-iodoindane-5-carbonitrile. LCMS calc.=270.0; found=270.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.78 (s, 1H), 7.48 (s, 1H), 2.96 (t, J=7.5 Hz, 2H), 2.92 (t, J=7.5 Hz, 2H), 2.16-2.10 (m, 2H).

후처리

  1. temperatureThe mixture was then heated at 80° C. under N2 for 2 h
  2. customThe reaction mixture was quenched with saturated Na2S2O3
  3. custompartitioned between CH2Cl2 and water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-db9018ef49c042158934b1e46d0db72c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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