Isoamyl Nitrite → 6-Iodoindane-5-carbonitrile

HRID 604611Notes

Reaction equation

HRID 604611 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 575762696-Iodoindane-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-db9018ef49c042158934b1e46d0db72c
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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