Potassium Hydroxide → 1-[3-(N-methylamino)phenyl]-1,3-butadiyne

HRID 1614382Notes

Reaction equation

HRID 1614382 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][CH3:14])[CH:8]=1.[OH-].[K+]>C1C=CC=CC=1>[CH3:14][NH:13][C:9]1[CH:8]=[C:7]([C:6]#[C:5][C:4]#[CH:3])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 197738175-hydroxy-5-methyl-1-[3-(N-methylamino)phenyl] hexa-1,3-diyne

Product 1

HCID 197738121-[3-(N-methylamino)phenyl]-1,3-butadiyneYield 42.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1600 mg of the thus-obtained diacetylene compound were then dissolved in 300 ml of benzene, and 450 mg of potassium hydroxide were then added to the reaction mixture, followed by reflux under heating for 1 hour. After filtration, the solvent was evaporated, and the residue was then purified by silica-gel column chromatography using benzene as an eluent to obtain 500 mg of 1-[3-(N-methylamino)phenyl]-1,3-butadiyne.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 1 hour
  3. filtrationAfter filtration
  4. customthe solvent was evaporated
  5. customthe residue was then purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-4d653716016949dbb1c9f7ae775772d6
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Reaction notes

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