Sodium Hydroxide → HCID 12640190, compound

HRID 1680448Notes

Reaction equation

HRID 1680448 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[O:14])=[N:11][CH:12]=1.[OH-:18].[Na+]>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:18])=[O:14])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12640219HCID 12640219, compound

Product 1

HCID 12640190HCID 12640190, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

4.93 g of 5-(m-chlorobenzylamino)-pyridine-2-carboxaldehyde are added in small portions to the cold stirring solution 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 yellow filtrate is cooled and 12 N hydrochloric acid is added until the pH is 5. A solid precipitates which is collected by filtration and crystallized from methanol, to yield the 5-(m-chlorobenzylamino)-pyridine-2-carboxylic acid melting at 170°-174°.

Workup

  1. additionis added
  2. filtrationfiltered
  3. temperatureThe yellow filtrate is cooled
  4. addition12 N hydrochloric acid is added until the pH is 5
  5. customA solid precipitates which
  6. filtrationis collected by filtration
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-a6865638986f415d805b38098e13dc95
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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