Hydrochloric Acid → (3-Chloropyridin-2-yl)methanol

HRID 46489Notes

Reaction equation

HRID 46489 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1.[ClH:14]>O.S>[Cl:14][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 15645802(3-Aminopyridin-2-yl)methanolHCID 23668193Sodium Nitrite

Product 1

HCID 10486967(3-Chloropyridin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 402Hydrogen SulfideSolventHCID 962WaterSolvent3×

Procedure

A solution of sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a mixture of 3-amino-2-hydroxymethylpyridine (4.8 g), aqueous hydrochloric acid (48%, 10 ml) and water (5 ml) stirred at 0°-5°. This solution was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and the mixture was heated on a steam-bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. The mixture was filtered, concentrated and extracted with chloroform and the chloroform extract was evaporated to give 3-chloro-2-hydroxymethylpyridine (3.7 g) m.p. 42°-44° (from n-pentane).

Workup

  1. temperaturethe mixture was heated on a steam-bath for 0.5 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. extractionthe chloroform extract
  6. customwas evaporated

Sources & evidence

ORD record
ord-d06799c8e7d2446093d305f30ce0c2ac
Source dataset
uspto-grants-1979_11
Patent number
US04173644

Reaction notes

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