Water → 8-(Benzyloxy)-2-methoxyquinoline

HRID 1777173Notes

Reaction equation

HRID 1777173 reaction equation
[CH3:1][O:2][Na].[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19](Cl)[CH:18]=[CH:17]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([O:2][CH3:1])[CH:18]=[CH:17]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 220422348-(Benzyloxy)-2-chloroquinolineHCID 178418582HCID 178418582, compound

Product 1

HCID 673664878-(Benzyloxy)-2-methoxyquinolineYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of MeONa (400 mg, 7.43 mmol) in MeOH (20 mL) was added 8-(benzyloxy)-2-chloroquinoline (2.0 g, 7.43 mmol). The mixture was stirred at 70° C. for 16 h. To the mixture was added H2O (20 mL) and the product extracted with toluene (30 mL×3). The combined organic layers were dried with Na2SO4 and evaporated to give the desired compound (1.5 g, yield 79%). LCMS (m/z): 266.1 [M+H]+

Workup

  1. extractionthe product extracted with toluene (30 mL×3)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-2f434faa36d14928a1537eebf082687d
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

Loading…