Dimethylformamide → 6-Aminopicolinonitrile

HRID 2169999Notes

Reaction equation

HRID 2169999 reaction equation
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[CH3:15][N:16](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:6]1[N:7]=[C:2]([C:15]#[N:16])[CH:3]=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 5642986-Aminopicolinonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
170 °C

Procedure

340 mg (2.89 mmol, 1 eq) of zinc cyanide are added to 500 mg (2.89 mmol, 1 eq) of 6-bromopyridin-2-ylamine in 10 ml of dimethylformamide in a microwave tube. 170 mg (0.147 mmol, 0.05 eq) of tetrakis(triphenylphosphine)palladium are added. The medium is heated at 170° C. for 1 hour 30 minutes in a microwave oven. 50 ml of ethyl acetate are added to the medium, which is filtered over celite. The filtrate is washed with water and extracted with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The residue is triturated in heptane. 6-Aminopyridine-2-carbonitrile is obtained in the form of an orange solid.

Workup

  1. filtrationis filtered over celite
  2. washThe filtrate is washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customThe residue is triturated in heptane

Sources & evidence

ORD record
ord-ca3e6d5242184798b09a0a4dbc81f5ce
Source dataset
uspto-grants-2015_06
Patent number
US09050266B2

Reaction notes

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