Hydrochloric Acid → 6-(Hydroxymethyl)pyridin-3-ol hydrochloride

HRID 443433Notes

Reaction equation

HRID 443433 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C(=O)C)=[CH:8][N:7]=1)(=O)C.[ClH:16]>CC(CC)=O>[ClH:16].[OH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2715886-(Acetoxymethyl)pyridin-3-yl acetate

Product 1

HCID 187584236-(Hydroxymethyl)pyridin-3-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

220.0 g of the above ester is added to 2,200 ml of 6N-hydrochloric acid and the resulting solution is refluxed for 18 hours. Then, the solution is evaporated to leave an oily viscous residue. This residue is digested with ethyl methyl ketone to yield 5-hydroxy-2-pyridinemethanol hydrochloride melting at 122°-123°. (The corresponding free base is prepared by adding a saturated solution of potassium carbonate to the hydrochloride, extracting the resulting suspension with chloroform, drying the chloroform extract over sodium sulfate, filtering and evaporating the filtrate to yield the free base.)

Workup

  1. temperaturethe resulting solution is refluxed for 18 hours
  2. customThen, the solution is evaporated
  3. customto leave an oily viscous residue

Sources & evidence

ORD record
ord-a97f9913d0b648d49bdeee3150ffad05
Source dataset
uspto-grants-1981_04
Patent number
US04260620

Reaction notes

Loading…