Sodium Methoxide → 8-(Benzyloxy)-2-methoxyquinoline

HRID 1782012Notes

Reaction equation

HRID 1782012 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:20][O-:21].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:13]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([O:21][CH3:20])[CH:11]=[CH:10]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 220422348-(Benzyloxy)-2-chloroquinoline

Product 1

HCID 673664878-(Benzyloxy)-2-methoxyquinolineYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

The crude 2-chloro-8-benzyloxyquinoline from above was dissolved in toluene (10 mL) and added to a stirred 25 wt % solution of NaOMe in MeOH (50 mL). The reaction solution was heated with stirring overnight at 70° C. After cooling to room temperature, the reaction solution was poured onto ice and extracted with toluene. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a colorless oil (6.14 g, 92%). The product was used without further purification.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction solution was poured onto ice
  4. extractionextracted with toluene
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa7e0147be2e4f0db41ecde21e4aadae
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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