Sodium Hydroxide → (6-Methylpyridin-3-yl)acetic acid

HRID 2369259Notes

Reaction equation

HRID 2369259 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9](N2CCOCC2)=S)=[CH:4][CH:3]=1.[OH-:17].[Na+].[OH2:19].CCO>>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:19])=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 2727779HCID 2727779, compoundHCID 19096565Water ethanol

Product 1

HCID 22507698(6-Methylpyridin-3-yl)acetic acid

Procedure

Crude 2-(6-Methyl-pyridin-3-yl)-1-morpholin-4-yl-ethanethione (39.5 mmol, 9.685 g) was suspended in 2:1 H2O/EtOH (75 cm3). NaOH (3.3 eq., 118.5 mmol, 4.8 g) added and the reaction heated to reflux for 16 hours. Volatiles were then removed from the cooled reaction medium, and the aqueous residue extracted with DCM (3×50 cm3). The pH was adjusted to precisely pH 7.0 with HCl, and a further DCM extraction performed (3×50 cm3). Water was removed from the residue, and the obtained solids slurried in methanol, filtered, and the filtrate evaporated to dryness. The orange solid obtained gave spectroscopic data consistent with the desired product. Mass recovery is typically >100% however this is due to NaCl within the product.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 16 hours
  3. customVolatiles were then removed from the cooled reaction medium
  4. extractionthe aqueous residue extracted with DCM (3×50 cm3)
  5. extractiona further DCM extraction
  6. customWater was removed from the residue
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness
  9. customThe orange solid obtained

Sources & evidence

ORD record
ord-c837319fb1694b448e9e86475f532451
Source dataset
uspto-grants-2014_04
Patent number
US08703952B2

Reaction notes

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