Potassium Cyanide → HCID 22054486, compound

HRID 1829745Notes

Reaction equation

HRID 1829745 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[C-:18]#[N:19].[K+]>C(#N)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[CH3:12][C:8]1[CH:7]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[C:10](=[CH:11][C:2]([C:18]#[N:19])=[CH:3][CH:4]=2)[N:9]=1

Participants

7

Reactant 2

HCID 9032Potassium CyanideHCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

Product 1

HCID 22054486HCID 22054486, compoundYield 75.2%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline (1.50 g, 4.43 mmol), potassium cyanide (578 mg, 8.87 mmol), tetrakis(triphenylphosphine)palladium(0) (256 mg, 0.22 mmol), and copper iodide (85 mg, 0.44 mmol) in acetonitrile (10 mL) was refluxed for 90 min. After cooling the mixture was diluted with ethyl acetate, filtered, and the filtrate was washed with brine, dried (Na2SO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) yielded the title compound (791 mg, 75%). Light brown solid, ISP-MS: m/e=238.3 ([M+H]+).

Workup

  1. temperaturewas refluxed for 90 min
  2. temperatureAfter cooling the mixture
  3. filtrationfiltered
  4. washthe filtrate was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3f4d21d3826942bc9a7bd868becabaaa
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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