3-Cyanopyridine → HCID 11019400, compound

HRID 359329Notes

Reaction equation

HRID 359329 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#N.Br[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].Cl.C([O:18]CC)C>[Cl-].[NH4+]>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]([CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[O:18])[CH:4]=1

Participants

6

Reactant 4

HCID 793-CyanopyridineHCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 78911-Bromo-3-methylbutane

Product 1

HCID 11019400HCID 11019400, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 3-cyanopyridine (26.0 g, 0.25 mole) in dry diethyl ether (200 ml) was added dropwise over the hour to the Grignard reagent prepared from 1-bromo-3-methyl butane (40.7 g, 0.27 mole) and magensium (6.8 g, 0.26 mole) in dry diethyl ether (50 ml) under nitrogen. The mixture was heated at 35°C. for eight hours, cooled to room temperature, and diluted with cold saturated aqueous ammonium chloride solution (200 ml) followed by concentrated hydrochloric acid (50 ml). The mixture was stirred for five hours, the ether layer separated, and the aqeuous layer boiled for two hours. The aqueous layer was neutralised to pH9 with aqueous sodium hydroxide solution and extracted with diethyl ether (3×100 ml. The organic phase was dried (magnesium sulphate), concentrated under reduced pressure and distilled to give 3-methylbutyl 3-pyridyl ketone.

Workup

  1. temperaturecooled to room temperature
  2. customthe ether layer separated
  3. waitthe aqeuous layer boiled for two hours
  4. extractionextracted with diethyl ether (3×100 ml
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. concentrationconcentrated under reduced pressure
  7. distillationdistilled

Sources & evidence

ORD record
ord-54c33f9fbab64054b3aef77e752863a2
Source dataset
uspto-grants-1991_03
Patent number
US05000946

Reaction notes

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