Methane → 2-Chloro-6-methylpyridin-3-ol

HRID 489263

Reaction equation

HRID 489263 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C.[ClH:10]>CO>[Cl:10][C:7]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]([CH3:8])[N:6]=1

Participants

5

Procedure

5-Hydroxy-2-methylpyridine (1-014-01) (27.01 g) was dissolved in conc. hydrochloric acid (200 mL) and to the reaction mixture was bubbled chlorine gass at 68 to 74° C. After the reaction mixture was stood overnight, the volatile was removed by bubbling nitrogen gas. The reaction mixture was evaporated under reduced pressure to give the crystal residue. The crystal residue was dissolved in methanol, and treated with active charcoal. After recrystallization, the desired 2-chloro-3-hyroxy-6-methylpyridine (1-014-02) (23.96 g, 67.3%) was obtained.

Workup

  1. customwas bubbled chlorine gass at 68 to 74° C
  2. customthe volatile was removed
  3. customby bubbling nitrogen gas
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customto give the crystal residue
  6. customAfter recrystallization

Sources & evidence

ORD record
ord-2b07074f87f74c3fa762d2f57ac48cfd
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Linked notes

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