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Benzyl Bromide → 5-(Benzyloxy)-N-methoxy-N-methylpyridine-2-carboxamide

HRID 573321
Notes
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Reaction equation

HRID 573321 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 866889815-hydroxy-N-methoxy-N-methylpicolinamide

Product 1

HCID 860606535-(Benzyloxy)-N-methoxy-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-hydroxy-N-methoxy-N-methylpicolinamide (7.51 g), K2CO3 (6.27 g) and benzyl bromide (2.83 mL) in acetone (70 mL) was stirred at 50° C. for 14 h, evaporated, treated with water and extracted with AcOEt. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to the title compound (4.87 g).

Workup

  1. customevaporated
  2. additiontreated with water
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane) to the title compound (4.87 g)

Sources & evidence

ORD record
ord-fdf50cba9e1c4550aa4db1c304129ce0
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes