Sodium Hydroxide → 6-[(Oxan-4-yl)oxy]pyridine-3-carboxylic acid

HRID 341541Notes

Reaction equation

HRID 341541 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[O:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66803133HCID 66803133, compound2×

Product 1

HCID 242295766-[(Oxan-4-yl)oxy]pyridine-3-carboxylic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-(oxan-4-yloxy)pyridine-3-carboxylate (Intermediate 236, 0.239 g, 0.95 mmol) was dissolved in EtOH (5 mL), 2M aq. sodium hydroxide (1.43 mL, 2.85 mmol) was added and the mixture was stirred at room temperature for 4 h. The mixture was concentrated under vacuum and the residue acidified to pH 6 by adding 2M aq. hydrochloric acid. The mixture was then extracted with DCM, followed by chloroform/isopropanol. The organic layer was separated using a hydrophobic frit and concentrated under vacuum to afford the title compound as a white solid (0.162 g, 47%), which was used directly in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=224 Found: m/z=224, Rt=1.06 min (91%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionby adding 2M aq. hydrochloric acid
  3. extractionThe mixture was then extracted with DCM
  4. customThe organic layer was separated
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c3670c1bf63e4ed59c92ed74235a0c4c
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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