Potassium Hydroxide → HCID 70578036, compound

HRID 1680452Notes

Reaction equation

HRID 1680452 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11](C(OC)=O)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:7][N:6]=1)=[O:4].[OH-].[K+]>O>[C:3]([OH:4])(=[O:2])[CH3:5].[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54294099HCID 54294099, compound

Product 1

HCID 70578036HCID 70578036, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 811 g of 5-(N-carbomethoxy-N-p-fluorobenzylamino)-pyridine-2-carboxylic acid methyl ester and 5,000 ml of 20% aqueous potassium hydroxide is refluxed for 5 hours while stirring under nitrogen. The solution is diluted with 12,000 ml of water, filtered and the filtrate acidified with 1,200 ml of 38% hydrochloric acid to pH=3.5 while cooling and stirring for an hour. The precipitate is collected, washed 4 times with a total of 2,000 ml of water and dried at 70° and 3 mm Hg. 1,351 g thereof are dissolved in 16,000 ml of boiling dioxane, the solution filtered, the filtrate concentrated to about 7,000 ml at 10 mm Hg and allowed to cool to room temperature while stirring. The crystals formed are collected and 1,046 g thereof dissolved in 5,000 ml of glacial acetic acid at 95%. The solution is allowed to stand overnight at room temperature, the precipitate collected and washed with 500 ml of glacial acetic acid, followed by 1,000 ml of diethyl ether, to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid acetate.

Workup

  1. temperatureis refluxed for 5 hours
  2. filtrationfiltered
  3. temperaturewhile cooling
  4. stirringstirring for an hour
  5. customThe precipitate is collected
  6. washwashed 4 times with a total of 2,000 ml of water
  7. customdried at 70°
  8. dissolution1,351 g thereof are dissolved in 16,000 ml of boiling dioxane
  9. filtrationthe solution filtered
  10. concentrationthe filtrate concentrated to about 7,000 ml at 10 mm Hg
  11. stirringwhile stirring
  12. customThe crystals formed
  13. customare collected
  14. dissolution1,046 g thereof dissolved in 5,000 ml of glacial acetic acid at 95%
  15. customthe precipitate collected
  16. washwashed with 500 ml of glacial acetic acid

Sources & evidence

ORD record
ord-82fff5db022b4a17a4d3e3906ed09b85
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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