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

HRID 1395188Notes

Reaction equation

HRID 1395188 reaction equation
C(O[C:5]1[C:10](C)=[CH:9][C:8]([O:12]C(=O)C)=[CH:7][N:6]=1)(=O)C.[ClH:16].C[C:18](CC)=[O:19]>>[ClH:16].[OH:12][C:8]1[CH:9]=[CH:10][C:5]([CH2:18][OH:19])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6569Methyl Ethyl KetoneHCID 705878932-Acetoxy-methyl-5-acetoxypyridine

Product 1

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

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-70ca9d2b19c6428db54c8f15c86c18d5
Source dataset
uspto-grants-1980_05
Patent number
US04202901

Reaction notes

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