Ethylenediamine → 6-Amino-4-methylnicotinonitrile

HRID 1441882

Reaction equation

HRID 1441882 reaction equation
Br[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:10]([Cu])#[N:11].C(N)CN>CC(N(C)C)=O>[NH2:8][C:5]1[CH:4]=[C:3]([CH3:9])[C:2]([C:10]#[N:11])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8176952-Amino-5-bromo-4-methylpyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 99641036-Amino-4-methylnicotinonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 5-bromo-4-methyl-pyridin-2-ylamine (500 mg, 2.67 mmol), CuCN (478 mg, 5.34 mmol) and DMA (2 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 851A (309 mg, 87%) 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-f1cda6e7b855453aba081b91d743fa7d
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Linked notes

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