Hydrochloric Acid → HCID 178524411, compound

HRID 1087920Notes

Reaction equation

HRID 1087920 reaction equation
[OH-].[Na+].[Cl:3][O-].[Na+].[OH:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].Cl>>[Cl:3][C:13]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:6])=[N:15][CH:14]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite2×HCID 178418543HCID 178418543, compound

Product 1

HCID 178524411HCID 178524411, compoundYield 81.8%

Procedure

To an agitated solution of 216.0 g of sodium hydroxide pellets in 2.25 liters of 5% (1.51 moles) sodium hypochlorite solution was added 150.1 g (1.08 mole) of 2-hydroxynicotinic acid. Temperature of the reaction mixture was 20° C. Four hours later 750 ml of 5% (0.50 mole) of sodium hypochlorite solution was added and stirring was continued overnight. The reaction mixture was mixed with 12N hydrochloric acid in an agitated vessel in such a manner that the receiving solution was always strongly acid and temperature was kept below 20° C. with an ice bath. The amount of 12N acid used was 600 ml. The mixture was readily filtered on a sintered glass suction funnel. The crystalline filter cake was washed with 800 ml of water followed by 800 ml of 1:1 isopropyl ether/isopropyl alcohol. Crystals were powdery when dry. The weight of dry crystals was 153.2 g (81.8% yield). Analysis by 1HNMR showed the dried product contained no starting material and contained about 5% of 3,5-dichloro-2-hydroxypyridine. See Example 3 for method of computing impurity.

Workup

  1. customwas 20° C
  2. customtemperature was kept below 20° C. with an ice bath
  3. filtrationThe mixture was readily filtered on a sintered glass suction funnel
  4. washThe crystalline filter cake was washed with 800 ml of water
  5. customdry

Sources & evidence

ORD record
ord-e0d3a7ff02ed4ab2aea7e43e378b0904
Source dataset
uspto-grants-1990_10
Patent number
US04960896

Reaction notes

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