Benzyl Bromide → HCID 178517714, compound

HRID 1398520Notes

Reaction equation

HRID 1398520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[C:2]=1[OH:8].[OH-].[K+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH2:11]([O:7][C:3]1[C:2]([OH:8])=[N:1][CH:6]=[CH:5][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 178516237HCID 178516237, compound

Product 1

HCID 178517714HCID 178517714, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine-2,3-diol (38 g, 342.04 mmol) was added to a solution of potassium hydroxide (21 g, 374.26 mmol) in methanol (400 mL) in portions while maintaining the reaction temperature below 30° C. Benzyl bromide (64.4 g, 376.53 mmol) was then added dropwise with stirring to the reaction mixture at room temperature. The resulting solution was stirred at 40° C. for 5 hr then concentrated in vacuo. The residue was diluted with water (500 mL) and the mixture was extracted with of dichloromethane (2×500 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Recrystallization from ethanol afforded the title compound (30 g, 43%) as a white solid: 1H NMR (400 MHz, DMSO) delta 11.60 (s, 1H), 7.45-7.28 (m, 5H), 6.96-6.89 (m, 2H), 6.10-6.06 (m, 1H), 5.01 (s, 2H).

Workup

  1. temperaturewhile maintaining the reaction temperature below 30° C
  2. stirringThe resulting solution was stirred at 40° C. for 5 hr
  3. concentrationthen concentrated in vacuo
  4. additionThe residue was diluted with water (500 mL)
  5. extractionthe mixture was extracted with of dichloromethane (2×500 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a80e7d1b7f4a482aa8dedc2c454ff7b7
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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