Benzyl Bromide → HCID 21107328, compound

HRID 1765548Notes

Reaction equation

HRID 1765548 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)[CH:4]=[CH2:5].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:3]([C:6]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21107316HCID 21107316, compound2×

Product 1

HCID 21107328HCID 21107328, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.7 g, 16.8 mmol) in anhydrous N,N-dimethylformamide (80 ml) was added 5-allyl-quinolin-6-ol (intermediate 5) (2.68 g, 14 mmol) slowly at room temperature. The reaction mixture was stirred for 1 hour, then benzyl bromide (2.57 ml, 21 mmol) was added. The mixture was allowed to stir for 1.5 hrs at room temperature, quenched with water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum. Chromatography (30% hexanes-ethyl acetate) afforded 3.6 g (92%) of 5-allyl-6-benzyloxy-quinoline as a light brown oil. MS ESI m/z 276 [M+H]+.

Workup

  1. stirringto stir for 1.5 hrs at room temperature
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-bb4c30f5ce0c4853956763fcced2dee6
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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