Benzyl Bromide → HCID 68830882, compound

HRID 1986447Notes

Reaction equation

HRID 1986447 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16]#[N:17])=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16]#[N:17])=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 51050240HCID 51050240, compound

Product 1

HCID 68830882HCID 68830882, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.5 g, 4.7 mmol) and benzyl bromide (0.61 g, 5.1 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (0.71 g, 5.1 mmol), and the mixture was stirred at room temperature for 17 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and water (100 ml). The aqueous layer was separated and extracted with ethyl acetate (50 ml). The organic layer and the extract were combined and the mixture was washed with saturated brine (50 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography, and crystallized from n-hexane-ethyl acetate to give 6-(benzyloxy)-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.7 g, yield 91%) as pale-yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and water (100 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (50 ml)
  4. washthe mixture was washed with saturated brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customcrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-ccb6f374a9144b12883502735a880dbd
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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