Cesium carbonate → Ethyl 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxylate

HRID 1896874Notes

Reaction equation

HRID 1896874 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=1.Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=3)[N:5]=[C:4]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178469289HCID 178469289, compound

Product 1

HCID 58562636Ethyl 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

An acetonitrile solution of ethyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate (50 g, 175 mmol) and 1-(chloromethyl)-4-methoxybenzene (33 ml, 245 mmol), is treated with Cs2CO3 (80 g, 245 mmol) and heated at 70° C. for 18 h. Salts were removed by filtration and the solvent removed under vacuum. The residue was dissolved in EtOAc and washed with water and sat NaCl. Organic layer dried over Na2SO4 and evaporated under vacuum. The resulting solid was recrystallized from EtOAc/Hex to give the title compound.

Workup

  1. customSalts were removed by filtration
  2. customthe solvent removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialOrganic layer dried over Na2SO4
  6. customevaporated under vacuum
  7. customThe resulting solid was recrystallized from EtOAc/Hex

Sources & evidence

ORD record
ord-f6ff1871e5244f418231b2399bed95f6
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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