3-Cyanopyridine → HCID 19756119, compound

HRID 1587704Notes

Reaction equation

HRID 1587704 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]C.C([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)#N.[Cl-].[NH4+].C([O:25][CH2:26][CH3:27])C>>[C:26]([C:20]1[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=1)(=[O:25])[CH2:27][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 5

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

Product 1

HCID 19756119HCID 19756119, compoundYield 58.3%

Procedure

To 50 ml of anhydrous ether was added 1.22 g of magnesium for Grignard reaction, and 11.0 g of 1-bromodecane was added to the mixture while stirring. After the magnesium was completely dissolved, a diethyl ether solution of 5.20 g (50 mmol) of 3-cyanopyridine was added dropwise, and the mixture 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 were combined, washed with water, and then dried over anhydrous sodium sulfate. After concentration under a reduced pressure, the residue was purified by separation by silica gel chromatography (ethyl acetate:hexane=1:4) to give 7.20 g of the desired product (yield 58.3%).

Workup

  1. additionwas added to the mixture
  2. temperaturethe mixture 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 residue was purified by separation by silica gel chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-b6a80de983af470a80f591817c09c9ad
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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