Hydrochloric Acid → 2-Methoxy-3-pyridineacetic acid

HRID 1837703Notes

Reaction equation

HRID 1837703 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]#N)=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-:12].[Na+].Cl.C[OH:16]>>[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]([OH:16])=[O:12])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 226785372-(2-Methoxypyridin-3-yl)acetonitrile

Product 1

HCID 226783192-Methoxy-3-pyridineacetic acid

Conditions

Temperature
100 °C

Procedure

2.2 g of (2-methoxy-3-pyridyl)methyl cyanide, 35 ml of a 1N aqueous sodium hydroxide and 35 ml of methanol were stirred under heating at 100° C. for 1.5 hours. The mixture was cooled to room temperature, and then, 35 ml of a 5N aqueous hydrochloric acid was added thereto, and the solvent was evaporated. Ethanol was added to the residue and a solid was filtered off. Ethanol was evaporated, and ethanol was added again to the residue and a solid was filtered off. Ethanol was evaporated, to give 2.4 g of white crystals.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was evaporated
  3. additionEthanol was added to the residue
  4. filtrationa solid was filtered off
  5. customEthanol was evaporated
  6. additionethanol was added again to the residue
  7. filtrationa solid was filtered off
  8. customEthanol was evaporated

Sources & evidence

ORD record
ord-35292d471e5d404ea43a0c9dea345650
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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