Sodium Bicarbonate → (6-Chloropyridin-2-yl)methanol

HRID 1975745Notes

Reaction equation

HRID 1975745 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[N:7]=1)(=O)C.C(=O)(O)[O-].[Na+]>Cl>[Cl:12][C:8]1[N:7]=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 107261902-Acetoxymethyl-6-chloropyridine

Product 1

HCID 182139(6-Chloropyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-acetoxymethyl-6-chloropyridine (17.3 g; 93.3 mmol), prepared as in step 2, in 250 mL 10% aqueous HCl was heated at reflux for 1.5 hours. The reaction mixture was cooled to room temperature and poured into 300 mL saturated aqueous sodium bicarbonate. The solution was adjusted to pH 9 by the addition of solid sodium bicarbonate. The solution was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated. The 6-chloro-2-hydroxymethylpyridine was used with no further purification.

Workup

  1. temperatureat reflux for 1.5 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe 6-chloro-2-hydroxymethylpyridine was used with no further purification

Sources & evidence

ORD record
ord-a9ff0ad75fd94571a8d3ff5d6b5da232
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

Loading…