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

HRID 1680459Notes

Reaction equation

HRID 1680459 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-:18].[Na+]>O.[N+]([O-])([O-])=O.[Ag+]>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:18])=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12640239HCID 12640239, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

4.62 g of 5-(p-fluorobenzylamino)-pyridine-2-carboxaldehyde are added in small portions to the cold stirring mixture consisting of 70.4 g of silver nitrate in 150 ml of water and 33.1 g of sodium hydroxide in 150 ml of water. The mixture is stirred 10 minutes after the last of the aldehyde is added and filtered. The filtrate is cooled, acidified with 12 N hydrochloric acid to a pH=4, filtered and the residue washed with water to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid melting at 197°-200°. The starting material is prepared as follows:

Workup

  1. additionis added
  2. filtrationfiltered
  3. temperatureThe filtrate is cooled
  4. filtrationfiltered
  5. washthe residue washed with water

Sources & evidence

ORD record
ord-0e95a887bd2f4c38b9d6fde2da82bf25
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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