Ethanol → 3-Methoxy-isonicotinic acid

HRID 2094500

Reaction equation

HRID 2094500 reaction equation
COC[C:4]1[CH:11]=[N:10][CH:9]=[CH:8][C:5]=1[C:6]#N.[OH-:12].[Na+].[CH2:14]([OH:16])C.[OH2:17]>>[CH3:14][O:16][C:4]1[CH:11]=[N:10][CH:9]=[CH:8][C:5]=1[C:6]([OH:17])=[O:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 58148255HCID 58148255, compound

Product 1

HCID 272824573-Methoxy-isonicotinic acid

Procedure

A mixture of 0.89 g of 3-methoxymethyl isonicotinonitrile, 0.72 g of sodium hydroxide, 6 ml of ethanol and 6 ml of water was heated to reflux for three hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. 3 M hydrochloric acid was added so that pH of the resultant residue became about 3. The reaction mixture was concentrated under reduced pressure. To the resultant solid, 40 ml of ethanol was added. The mixture was heated to reflux for five minutes, and subjected to hot filtration. The solid collected by filtration was subjected to the same operation twice by using 40 ml each of ethanol. Combined filtrates were concentrated to give 1.0 g of 3-methoxy isonicotinic acid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for three hours
  3. concentrationconcentrated under reduced pressure
  4. addition3 M hydrochloric acid was added so that pH of the resultant residue
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionTo the resultant solid, 40 ml of ethanol was added
  7. temperatureThe mixture was heated
  8. temperatureto reflux for five minutes
  9. filtrationsubjected to hot filtration
  10. filtrationThe solid collected by filtration
  11. concentrationCombined filtrates were concentrated

Sources & evidence

ORD record
ord-43e06be3b5a2485a8dab2f7261784567
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Linked notes

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