Acetic Anhydride → HCID 15163462, compound

HRID 845535Notes

Reaction equation

HRID 845535 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N+:6]([O-])=[C:5]([CH3:12])[C:4]=1[CH3:13].C(OC(=O)C)(=[O:16])C>>[OH:16][CH2:12][C:5]1[C:4]([CH3:13])=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 15163460HCID 15163460, compound

Product 1

HCID 15163462HCID 15163462, compoundYield 89%

Conditions

Temperature
80 °C

Procedure

4.5 g of 4,5-dimethoxy-2,3-dimethylpyridine 1-oxide are warmed to 110° C. in 20 ml of acetic anhydride in the course of 30 minutes and the mixture is then concentrated on a rotary evaporator. The oily residue, which consists of the intermediate 2-acetoxymethyl-4,5-dimethoxy-3-methylpyridine, is stirred in 30 ml of 3N sodium hydroxide solution at 80° C. for 2 hours, the mixture is extracted, after cooling, five times with 30 ml of methylene chloride each time, the combined organic phases are washed twice with 2N sodium hydroxide solution, dried and concentrated and the residue is stirred with petroleum ether, filtered off with suction and dried. 4.0 g (89% of theory) of 2-hydroxymethyl-4,5-dimethoxy-3-methylpyridine of m.p. 91°-92° C. are obtained.

Workup

  1. concentrationthe mixture is then concentrated on a rotary evaporator
  2. extractionthe mixture is extracted
  3. temperatureafter cooling
  4. washfive times with 30 ml of methylene chloride each time, the combined organic phases are washed twice with 2N sodium hydroxide solution
  5. customdried
  6. concentrationconcentrated
  7. stirringthe residue is stirred with petroleum ether
  8. filtrationfiltered off with suction
  9. customdried

Sources & evidence

ORD record
ord-dd09d15058e64bc0bcb46b756a5cc3cb
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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