3-Cyanopyridine → HCID 19756112, compound

HRID 1587698Notes

Reaction equation

HRID 1587698 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)#N.[Cl-].[NH4+].C([O:25]CC)C>>[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 5

HCID 793-CyanopyridineHCID 3283Diethyl Ether2×HCID 81731-BromodecaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×

Product 1

HCID 19756112HCID 19756112, compoundYield 32.9%

Procedure

To anhydrous ether was added 3.60 g of magnesium for Grignard reaction, and 36.5 g of 1-bromodecane was dropwise added while stirring. After the magnesium was completely dissolved, a diethyl ether solution of 15.6 g (0.15 mol) of 3-cyanopyridine was dropwise added and the mixture was refluxed for 4 hours. After cooling, saturated ammonium chloride solution was added, the diethyl ether layer was separated, and the aqueous layer was further extracted with diethyl ether. The ether layers was combined, washed with water, and then dried over anhydrous sodium sulfate. After concentration under a reduced pressure, the product was purified by separation by silica gel chromatography (ethyl acetate:hexane=1:4) to obtain 12.2 g of the desired product (yield 32.9%).

Workup

  1. additionwas dropwise added
  2. temperaturethe mixture was refluxed for 4 hours
  3. temperatureAfter cooling
  4. customthe diethyl ether layer was separated
  5. extractionthe aqueous layer was further extracted with diethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationAfter concentration under a reduced pressure
  9. customthe product was purified by separation by silica gel chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-914646cfe0f0458ba64e978316ac4b21
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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