Jineol → 3,8-Dimethoxy quinoline

HRID 399742Notes

Reaction equation

HRID 399742 reaction equation
[CH:1]1[CH:10]=[C:9]([OH:11])[C:8]2[N:7]=CC(O)=[CH:4][C:3]=2[CH:2]=1.[N+](=[CH2:15])=[N-].C[CH2:17][O:18][CH2:19][CH3:20]>C(O)C>[CH3:17][O:18][C:19]1[CH:20]=[N:7][C:8]2[C:3]([CH:4]=1)=[CH:2][CH:1]=[CH:10][C:9]=2[O:11][CH3:15]

Participants

4

Reactant 2

HCID 177338JineolHCID 21186548Diazomethane diethylether

Product 1

HCID 105837983,8-Dimethoxy quinolineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Jineol of 4.5 mg was dissolved in 2 ml of ethanol, and diazomethane ether solution was slowly dropped to the solution. After the excess of diazomethane and solvent was removed by purging with nitrogen gas, the solution was purified by silicagel chromatography to give 4.2 mg of 3,8-dimethoxy quinoline with 80% yield.

Workup

  1. customAfter the excess of diazomethane and solvent was removed
  2. customby purging with nitrogen gas
  3. customthe solution was purified by silicagel chromatography

Sources & evidence

ORD record
ord-a3d35d944aca43608a8e9c356519b602
Source dataset
uspto-grants-1998_10
Patent number
US05824689

Reaction notes

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