Potassium Hydroxide → 5-{[(4-Fluorophenyl)methyl]amino}pyridine-2-carboxylic acid

HRID 1680455Notes

Reaction equation

HRID 1680455 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14](N)=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-:19].[K+]>C(O)CC.O>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:19])=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12640217HCID 12640217, compound

Product 1

HCID 126401915-{[(4-Fluorophenyl)methyl]amino}pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent2×

Procedure

0.245 g of 5-(p-fluorobenzylamino)-pyridine-2-carboxamide are dissolved in 2.5 ml of warm n-propanol, the solution is combined with 2.5 ml of 20% aqueous potassium hydroxide and the mixture is heated on a steam bath for 16 hours. It is diluted with water and most of the n-propanol removed with a stream of nitrogen. The hot solution is filtered and the pH of the filtrate adjusted to 4 with hydrochloric acid. The precipitate formed is collected, redissolved in aqueous sodium bicarbonate, the solution filtered and reacidified with hydrochloric acid to pH=4. The solid formed is collected and air-dried, to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid melting at 196°-198°.

Workup

  1. temperaturethe mixture is heated on a steam bath for 16 hours
  2. customremoved with a stream of nitrogen
  3. filtrationThe hot solution is filtered
  4. customThe precipitate formed
  5. customis collected
  6. dissolutionredissolved in aqueous sodium bicarbonate
  7. filtrationthe solution filtered
  8. customThe solid formed
  9. customis collected
  10. customair-dried

Sources & evidence

ORD record
ord-f09226743e134c4aa27bb16adbc4433d
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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