Ethylenediamine → 6-Amino-4,5-dimethyl-3-pyridinecarbonitrile

HRID 2110504Notes

Reaction equation

HRID 2110504 reaction equation
Br[C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:11]([Cu])#[N:12].C(N)CN>CC(N(C)C)=O>[NH2:8][C:5]1[C:4]([CH3:9])=[C:3]([CH3:10])[C:2]([C:11]#[N:12])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 70103075-Bromo-3,4-dimethylpyridin-2-amineHCID 178418546HCID 178418546, compound

Product 1

HCID 218752066-Amino-4,5-dimethyl-3-pyridinecarbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 5-bromo-3,4-dimethyl-pyridin-2-ylamine (500 mg, 2.49 mmol), CuCN (445 mg, 4.97 mmol) and DMA (3.5 mL) was stirred under nitrogen for 20 h at 170° C. The reaction mixture was cooled and added to 50 mL of a 20% aqueous solution of ethane-1,2-diamine. The layers were separated and the aqueous layer was extracted 3× with EtOAc. The combined organics were washed with water, followed by brine and dried over MgSO4. Concentration in vacuo afforded compound 850A (362 mg, 99%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted 3× with EtOAc
  4. washThe combined organics were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-d41ed12a865c4b4fb5def960ecd978a3
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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