Pyridine-2-carbonitrile → HCID 178506282, compound

HRID 558034Notes

Reaction equation

HRID 558034 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[NH2:9][NH2:10].[F:11][C:12]([F:19])([F:18])[C:13](OCC)=O>C(O)C.CCOCC>[F:11][C:12]([F:19])([F:18])[C:13]1[NH:2][C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 7522Pyridine-2-carbonitrile2×HCID 9321HydrazineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 178506282HCID 178506282, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-cyanopyridine (1.04 g, 10.0 mmol) is placed in a 25 ml round-bottomed flask and ethanol is added into 2-cyanopyridine. After completly dissolved, hydrazine (0.96 g, 30.0 mmol) is added. At the room temperature, the reaction is carried out for 12 hrs. White solids are obtained. Ether is used to rinse the solids in order to remove the unreacted hydrazine. The white solids are placed in a 25 ml round-bottomed flask and added with ethyl 2,2,2-trifluoroacetate (1.42 g, 10.0 mmol). 5.0 ml of ethanol is added and then hot reflux is performed for 12 hrs. After the reaction is finished, ether extraction is carried out and the organic layer is collected and then concentrated to obtain white solids. After purified by silicone chromatographic column, the product tfpytz is obtained. The yield is about 50%. 1H NMR (500 MHz, CDCl3): δ 8.78 (m, 1 H), 8.31 (d, 1 H, J=8.0 Hz), 7.97˜7.94 (m, 1 H), 7.53˜7.50 (m, 1 H). HRMS (EI) m/z:calculated value C8H5F3N4 214.0466; experimental value 214.0469.

Workup

  1. dissolutionAfter completly dissolved
  2. customWhite solids are obtained
  3. washto rinse the solids in order
  4. customto remove the unreacted hydrazine
  5. customThe white solids are placed in a 25 ml round-bottomed flask
  6. temperaturehot reflux
  7. waitis performed for 12 hrs
  8. extractionether extraction
  9. customthe organic layer is collected
  10. concentrationconcentrated
  11. customto obtain white solids
  12. customAfter purified by silicone chromatographic column
  13. customthe product tfpytz is obtained

Sources & evidence

ORD record
ord-9b0987b25ecb488e9d1f1391f75bab5b
Source dataset
uspto-grants-2011_11
Patent number
US08062767B2

Reaction notes

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