N,N'-Dimethylethylenediamine → 3,4-Dimethoxybenzonitrile

HRID 2253503Notes

Reaction equation

HRID 2253503 reaction equation
[C-]#N.[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[CH3:15][NH:16]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH3:12])[C:15]#[N:16]

Participants

9

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 748423,4-Dimethoxybenzonitrile

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 (107 mg, 2.184 mmol), dried KI (60 mg, 0.361 mmol, 20 mol %) and CuI (34 mg, 0.210 mmol, 10 mol %), evacuated and backfilled with argon three times. 1-Bromo-3,4-dimethoxybenzene (260 μL, 1.807 mmol), N,N′-dimethylethylenediamine (195 μL, 1.832 mmol) and anhydrous toluene (1.2 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 washed with 1 mL of water and dried over MgSO4. The GC analysis showed complete conversion of starting material with formation of the title product (confirmed by GC-MS).

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. washthe organic layer was washed with 1 mL of water
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9aafa998ba5f431a894cee639d1a9a4a
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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