Isoamyl Nitrite → 6-Iodoindane-5-carbonitrile

HRID 604611ノート

反応式

HRID 604611 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 575762696-Iodoindane-5-carbonitrile

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-db9018ef49c042158934b1e46d0db72c
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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