Dimethylformamide → 8-Methylquinoline-5-carbonitrile

HRID 1172676Notes

Reaction equation

HRID 1172676 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](C)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cu]C#N.[CH3:16][N:17]([CH3:20])C=O>>[CH3:2][C:3]1[C:20]2[N:17]=[CH:16][CH:9]=[CH:8][C:7]=2[C:6]([C:11]#[N:10])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 45097734Quinoline, 8-bromo-5-methyl- (9CI)HCID 178418546HCID 178418546, compound

Product 1

HCID 129507888-Methylquinoline-5-carbonitrile

Conditions

Temperature
200 °C

Procedure

4.0 g 8-Bromo-5-methyl-quinoline and 1.69 g copper (I) cyanide were dissolved in 16 ml dimethylformamide and stirred at 200° C. for thirty minutes under microwave irradiation. The cooled reaction mixture was poured in 50 ml 2N HCL and extracted with 100 ml ethyl acetate. The organic layer was washed with 50 ml 2N HCl and 30 ml brine and then dried over MgSO4. The solvent was removed in vacuo. The resulting residue was purified on silica gel with the eluent n-heptane ethyl acetate=2:1 to obtain 3.0 g 8-Methyl-quinoline-5-carbonitrile.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured in 50 ml 2N HCL
  3. extractionextracted with 100 ml ethyl acetate
  4. washThe organic layer was washed with 50 ml 2N HCl and 30 ml brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customThe resulting residue was purified on silica gel with the eluent n-heptane ethyl acetate=2:1

Sources & evidence

ORD record
ord-d0afee40d7304e688acbb009e5e7f749
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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