Potassium Carbonate → 1-Ethynyl-2-methoxybenzene

HRID 1814479Notes

Reaction equation

HRID 1814479 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]#[C:10]C1C=CC(OC)=CC=1C=O.Cl.NO.C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])#[CH:10]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 225030652-[2-(2-Methoxyphenyl)-ethynyl]-5-methoxybenzaldehyde

Product 1

HCID 5829121-Ethynyl-2-methoxybenzeneYield 127.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[2-(2-Methoxyphenyl)-ethynyl]-5-methoxybenzaldehyde (0.95 g), hydroxylamine hydrochloride (0.25 g) and sodium acetate (0.32 g) were reacted in ethanol (20 ml) at 60° C. for 2 hr. Potassium carbonate (0.6 g) and water (2 ml) were added to the reaction mixture, and the mixture was heated under reflux for 12 hr. The reaction solution was evaporated, and then the resulting residue was extracted with methylene chloride, washed with brine and dried. The solvent was removed, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.60 g of the title compound as a yellowish brown amorphous. (232-4) 1-Chloro-7-methoxy-3-(2-methoxyphenyl)isoquinoline

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hr
  3. customThe reaction solution was evaporated
  4. extractionthe resulting residue was extracted with methylene chloride
  5. washwashed with brine
  6. customdried
  7. customThe solvent was removed
  8. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-ad56733f83d14c14800aef62f052aa63
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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