Hydrochloric Acid → 6-(Pyridin-2-yloxymethyl)-pyridine-3-carbaldehyde

HRID 1891870Notes

Reaction equation

HRID 1891870 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:10][CH:11]=1.CS(C)=O.Cl.[OH-].[Na+]>O1CCCC1>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:9]1[N:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 592553385-[1,3]Dioxolan-2-yl-2-(pyridin-2-yloxymethyl)-pyridine

Product 1

HCID 592553126-(Pyridin-2-yloxymethyl)-pyridine-3-carbaldehydeYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[1,3]dioxolan-2-yl-2-(pyridin-2-yloxymethyl)-pyridine (1.51 g, 5.85 mmol) described in Manufacturing Example 154-1-5 in tetrahydrofuran (15 mL) and dimethyl sulfoxide (10 mL) was added a 5 N hydrochloric acid aqueous solution (3 mL), which was stirred for 25 minutes at room temperature, and then for another 1 hour at 20 minutes at 60° C. A 5 N sodium hydroxide aqueous solution was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (603 mg, 48%).

Workup

  1. waitfor another 1 hour at 20 minutes at 60° C
  2. extractionwhich was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b7a856bc15724a9784f57251a568a5d2
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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