Propionitrile → HCID 59371251, compound

HRID 1915024Notes

Reaction equation

HRID 1915024 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]3[CH:15]=[CH:14][CH:13]=[CH:12][C:6]3=[CH:7][CH:8]=2)[N:3]=1.[Br:16][Si](C)(C)C.C(#N)CC.[OH-].[Na+]>>[Br:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]3[CH:15]=[CH:14][CH:13]=[CH:12][C:6]3=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 4

HCID 7854PropionitrileHCID 14798Sodium HydroxideHCID 76113BromotrimethylsilaneHCID 3275112-chlorobenzo[h]quinoline

Product 1

HCID 59371251HCID 59371251, compoundYield 96%

Procedure

A mixture of 2-chlorobenzo[h]quinoline (2.43 g, 11.4 mmol), bromotrimethylsilane (3.00 ml, 22.7 mmol) and propionitrile (12 ml) was heated under reflux for 111 hours. The reaction mixture was then poured into a 10% NaOH solution containing ice. The organic phase was separated and the aqueous phase extracted with Et2O (3×15 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by chromatography (SiO2, petroleum ether/acetate=9/1) to give 2-bromobenzo[h]quinoline in the form of a yellow solid: 2.82 g (96% yield); melting point: 113-114° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 111 hours
  3. additioncontaining ice
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted with Et2O (3×15 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue was purified by chromatography (SiO2, petroleum ether/acetate=9/1)

Sources & evidence

ORD record
ord-acbafa45c69b45a0b232d3f0e059c0b4
Source dataset
uspto-grants-2013_12
Patent number
US08614322B2

Reaction notes

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