Water → HCID 86707439, compound

HRID 338897Notes

Reaction equation

HRID 338897 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[CH:8]2.[C-:14]#[N:15].[Na+].O.CCOCC>CS(C)=O>[CH3:13][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:3]([CH2:2][C:14]#[N:15])[CH:4]=[CH:5][CH:6]=2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 86707438HCID 86707438, compound

Product 1

HCID 86707439HCID 86707439, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 8-(bromomethyl)-2-methylquinoline (1.50 g, 6.35 mmol) in DMSO (20 mL) was added NaCN (0.62 g, 12.7 mmol). The mixture was stirred at ambient temperature for 10 minutes. Water (100 mL) and ether (100 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate) to give 2-(2-methylquinolin-8-yl)acetonitrile (0.75 g, 58.3%) as a solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9f34468b5f6a42f0b4ef910d043c8b29
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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