Benzyl Bromide → HCID 57421820, compound

HRID 1784931Notes

Reaction equation

HRID 1784931 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:11]([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:11])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 340375-Hydroxynicotinic acid

Product 1

HCID 57421820HCID 57421820, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 818 mg (5.34 mmol) of 5-hydroxynicotinic acid, 1.70 g (12.3 mmol) of K2CO3, and 1.0 mL (8.41 mmol) of benzyl bromide in 25 mL of DMF was heated at 60° C. under Ar for 16 h. The mixture was filtered through cotton, and the residue was dissolved in CHCl3. The organic layer was washed with water (2×30 mL), brine (30 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography provided 363 mg of methyl 5-(benzyloxy)nicotinate in 28% yield as an orange oil.

Workup

  1. filtrationThe mixture was filtered through cotton
  2. dissolutionthe residue was dissolved in CHCl3
  3. washThe organic layer was washed with water (2×30 mL), brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-ef88394f1bbb4e17902870fb7589167d
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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