Hydrochloric Acid → HCID 12640243, compound

HRID 1680457Notes

Reaction equation

HRID 1680457 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]([OH:16])=[O:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(OO)(=[O:21])C.Cl>O.[OH-].[Na+]>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[N+:12]([O-:21])[C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6585Peracetic Acid2×HCID 126401915-{[(4-Fluorophenyl)methyl]amino}pyridine-2-carboxylic acid

Product 1

HCID 12640243HCID 12640243, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

5.77 g of 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid are dissolved in 40 ml of water and 20 ml of 2 N aqueous sodium hydroxide. The solution is stirred at room temperature and 3.6 g of 40% aqueous peracetic acid are added. The solution becomes green and within less than a minute a solid separates. Another 3.6 g of said peracetic acid are added and the mixture is stirred for 4 hours. The pH of the mixture is adjusted to 4 with hydrochloric acid and filtered after cooling. The solid is collected and recrystallized from 90% aqueous acetonitrile, to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid N-oxide melting at 206°-209°.

Workup

  1. stirringthe mixture is stirred for 4 hours
  2. filtrationfiltered
  3. temperatureafter cooling
  4. customThe solid is collected
  5. customrecrystallized from 90% aqueous acetonitrile

Sources & evidence

ORD record
ord-a576b0cbc33843b482784f84646db573
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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