Hydrochloric Acid → (3-Bromo-4-methylpyridin-2-yl)methanol

HRID 1855854Notes

Reaction equation

HRID 1855854 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[CH3:8].O.C([OH:14])C.Cl>C(OC(=O)C)(=O)C>[Br:1][C:2]1[C:3]([CH2:10][OH:14])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19096565Water ethanolHCID 233492233-Bromo-2,4-dimethylpyridine 1-oxide

Product 1

HCID 23344241(3-Bromo-4-methylpyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

3-Bromo-2,4-dimethylpyridine-N-oxide (14.7 g) in warm acetic anhydride (150 ml) was added dropwise to acetic anhydride (500 ml) at 125° and the mixture was refluxed for 1/2 hour, allowed to cool and then poured into water/ethanol (4:1, 500 ml). The solution was acidified with dilute hydrochloric acid and evaporated to dryness. The residue was refluxed with 2 N hydrochloric acid (100 ml) for 1 hour, cooled and extracted with chloroform. The aqueous phase was adjusted to pH 12 with sodium hydroxide and was extracted with chloroform, and this chloroform extract was evaporated to a residue which was crystallised from n-hexane to give 3-bromo-2-hydroxymethyl-4-methylpyridine (5.8 g) m.p. 75°-77°.

Workup

  1. temperaturethe mixture was refluxed for 1/2 hour
  2. temperatureto cool
  3. customevaporated to dryness
  4. temperatureThe residue was refluxed with 2 N hydrochloric acid (100 ml) for 1 hour
  5. temperaturecooled
  6. extractionextracted with chloroform
  7. extractionwas extracted with chloroform
  8. extractionthis chloroform extract
  9. customwas evaporated to a residue which
  10. customwas crystallised from n-hexane

Sources & evidence

ORD record
ord-4ed85e81007345ffbf6bce937bb955c3
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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