N,N'-Dimethylethylenediamine → (1,1'-Biphenyl)-2-carbonitrile

HRID 2253499Notes

Reaction equation

HRID 2253499 reaction equation
[C-]#N.[Na+].Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:17][NH:18]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:6]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:17]#[N:18])=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 163292-Bromobiphenyl

Product 1

HCID 141162(1,1'-Biphenyl)-2-carbonitrileYield 68%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

An oven dried screw cap test tube was charged with NaCN (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (29 mg, 0.152 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromobiphenyl (270 μL, 1.566 mmol), N,N′-dimethylethylenediamine (170 μL, 1.597 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The combined organic layers were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 190 mg (68% yield) of the title compound as a colorless oil.

Workup

  1. customAn oven dried screw
  2. customcap test tube
  3. customevacuated
  4. customThe tube was sealed
  5. temperatureThe resulting yellow suspension was cooled to room temperature
  6. stirringThe mixture was stirred at 25° C. for 10 min
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted three times with ethyl acetate (3×2 mL)
  9. washThe combined organic layers were washed with 5 mL of water
  10. dry with materialdried over MgSO4
  11. customThe solvent was removed at reduced pressure
  12. customPurification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-7f2fd129dc224dfc976167d78da0d806
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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