Water → 5-Cyanoquinoline

HRID 710477Notes

Reaction equation

HRID 710477 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:12]([Cu])#[N:13].[C-]#N.[Na+].O>CN(C=O)C.CCOC(C)=O>[C:12]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)#[N:13]

Participants

7

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 220249805-IodoquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 47150285-CyanoquinolineYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-iodoquinoline (0.56 g; 2.2 mmol) and CuCN (0.51 g; 5.7 mmol) in anhydrous DMF (3 ml) was refluxed for 40 min under N2. After cooling to room temperature, the mixture was diluted to 20 ml with EtOAc and NaCN (0.75 g; 15.3 mmol) was added followed by H2O (10 ml). The resulting mixture was vigorously stirred for 10 min and organic phase was separated, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.33 g; 97%) as colourless solid. 1H-NMR (CDCl3) 7.59-7.63 (m, 1H); 7.78 (m, 1H); 7.98 (dd, 1H, J=3, 6 Hz); 8.36 (d, 1H, J=9 Hz); 8.54 (m, 1H): 9.05 (dd, 1H, J=3, 6 Hz).

Workup

  1. temperaturewas refluxed for 40 min under N2
  2. additionwas added
  3. customorganic phase was separated
  4. washwashed with H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-eac43da1968942e88acade790e4c5c29
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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