Hydrochloric Acid → HCID 178524411, compound

HRID 1087921Notes

Reaction equation

HRID 1087921 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 76.6%

Procedure

To an agitated solution of 216.0 g of sodium hydroxide pellets in 2.25 liters of 5% (1.51 moles) of sodium hypochlorite solution was added 150.4 g of 2-hydroxynicotinic acid. Temperature of the reaction mixture was 19° C. Three hours later 750 ml (0.50 mole) of sodium hypochlorite 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 600 ml of water followed by 800 ml of 1:1 isopropyl ether/isopropyl alcohol. Weight of the dry crystals was 143.5 g (76.6% yield). Analysis by 1HNMR analysis showed the dried product contained no starting material and about 5% 3,5 -dichloro-2-hydroxypyridine. See Example 3 for method of computing impurity.

Workup

  1. customwas 19° 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 600 ml of water

Sources & evidence

ORD record
ord-cf4aa2ba587345ed8ddadf30767f02f3
Source dataset
uspto-grants-1990_10
Patent number
US04960896

Reaction notes

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