Hydrochloric Acid → 2-Amino-5-chloropyridin-3-ol

HRID 258566

Reaction equation

HRID 258566 reaction equation
[NH2:1][C:2]1[C:7](Cl)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH-:10].[K+].Cl.[Cl-].[Na+]>[Cu].COCCOCCOC>[NH2:1][C:2]1[C:7]([OH:10])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 778863,5-Dichloro-3-pyridylamine

Product 1

HCID 103132002-Amino-5-chloropyridin-3-olYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8150DiglymeSolvent

Procedure

A mixture of 20 parts of 2-amino-3,5-dichloropyridine, 160 parts of glycol, 80 parts of potassium hydroxide, 1 part of copper powder and 3 parts of diethylene glycol dimethyl ether is stirred under nitrogen for 5 hours at 150°-160° C. The cooled solution is neutralised with conc. hydrochloric acid, saturated with sodium chloride and extracted twice in the warm state with ethyl acetate. The combined extracts are filtered through Hyflo, dried over magnesium sulphate and purified with active charcoal. The solvent is evaporated off to leave 12.3 parts (70% of theory) of 2-amino-3-hydroxy-5-chloropyridine, m.p. 198°-201° C.

Workup

  1. extractionextracted twice in the warm state with ethyl acetate
  2. filtrationThe combined extracts are filtered through Hyflo
  3. dry with materialdried over magnesium sulphate
  4. custompurified with active charcoal
  5. customThe solvent is evaporated off

Sources & evidence

ORD record
ord-7b568c3df9f444d6a72ba2742e3cce12
Source dataset
uspto-grants-1977_07
Patent number
US04033975

Linked notes

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