Hydrochloric Acid → 2-Hydroxyisonicotinic Acid

HRID 626184Notes

Reaction equation

HRID 626184 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[OH-:11].[K+].Cl>O>[O:11]=[C:2]1[CH:3]=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][NH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2807562-Hydroxyisonicotinic AcidYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-chloroisonicotinic acid (15 g, 1.0 eq) in 200 mL water at 0° C. was added KOH (40 g, 7.5 eq). Then the reaction mixture was heated to reflux for 36 h., cooled, and 3 N HCl (aq) was added to pH=1˜3. The precipitate was collected by filtration and washed with water to give the product as a white solid (13.1 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.80 (brs, 2H), 7.47 (d, J=6.4 Hz, 1H), 6.79 (s, 1H), 6.50 (dd, J=6.8 Hz, 1.6 Hz, 1H).

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux for 36 h.
  3. temperaturecooled
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-ca207fc1239e458f96b8f687f711e382
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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