Benzyl Bromide → HCID 54220218, compound

HRID 1887233Notes

Reaction equation

HRID 1887233 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[OH-].[K+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH2:11]([O:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 994562,5-Dihydroxypyridine

Product 1

HCID 54220218HCID 54220218, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-hydroxypyridin-2(1H)-one (4.44 g, 40.0 mmol) in methanol (50 mL) was added potassium hydroxide (2.64 g, 40.0 mmol). The reaction mixture was stirred for 30 minutes at ambient temperature, followed by the addition of benzyl bromide (5.2 mL, 44 mmol). The reaction mixture was kept stirring at ambient temperature for 2 hours and then heated at 45-50° C. for 1 hour. The solvent was removed in vacuo, and the residue was washed with water, dichloromethane and then recrystallized from methanol to afford the title compound (5.39 g, 67%): 1H NMR (300 MHz, DMSO-d6) δ 11.08 (s, 1H), 7.42-7.26 (m, 6H), 7.09 (d, J=3.0 Hz, 1H), 6.30 (d, J=9.6 Hz, 1H), 4.89 (s, 2H); MS (ES+) m/z 202.3 (M+1).

Workup

  1. stirringThe reaction mixture was kept stirring at ambient temperature for 2 hours
  2. temperatureheated at 45-50° C. for 1 hour
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with water, dichloromethane
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5f3dd6b78c2a4d53bb30f83a1ce9903a
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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