Benzyl Bromide → HCID 23159744, compound

HRID 1011425Notes

Reaction equation

HRID 1011425 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[N:7]2.C([O-])([O-])=O.[Na+].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[CH2:23]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[N:7]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 135618214ethyl 5-hydroxyquinoline-3-carboxylate

Product 1

HCID 23159744HCID 23159744, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 5-hydroxyquinoline-3-carboxylate (2.17 g, 10 mmol) prepared in stage D of example 2, Na2CO3 (2.12 g, 20 mmol) and benzylbromide (1.71 g, 10 mmol) in DMF (20 mL) was stirred for 12 hours at room temperature. The reaction mixture was diluted with water (50 mL) and then extracted with AcOEt (3×25 mL). The combined organic layers were washed water, and dried over Magnesium sulfate and evaporated under reduced pressure. The obtained residue was chromatographed over silica-gel.

Workup

  1. extractionextracted with AcOEt (3×25 mL)
  2. washThe combined organic layers were washed water
  3. dry with materialdried over Magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe obtained residue was chromatographed over silica-gel

Sources & evidence

ORD record
ord-b6cf759d46af4eefb72a608bfe7a8487
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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