Hydrochloric Acid → methyl 5,6-dichloropyridine-2-carboxylate-N-oxide

HRID 1837437Notes

Reaction equation

HRID 1837437 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[N+:6]([O-:9])[C:5]([C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.Cl.[CH3:14]O>>[Cl:1][C:2]1[C:7]([Cl:8])=[N+:6]([O-:9])[C:5]([C:10]([O:12][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 129936895,6-dichloropyridine-2-carboxylic acid-N-oxide

Product 1

HCID 12993690methyl 5,6-dichloropyridine-2-carboxylate-N-oxide

Conditions

Temperature
45 °C

Procedure

A suspension of 5,6-dichloropyridine-2-carboxylic acid-N-oxide (5.0 g, 24.0 mmol) in methanol (100 mL) was saturated with HCl gas and the reaction mixture heated at 40-50° C. for one hour. The solvent was removed and the residue dissolved in diethyl ether/ethyl acetate. The organic solution was washed with water, saturated sodium bicarbonate solution, brine, dried, and concentrated to give methyl 5,6-dichloropyridine-2-carboxylate-N-oxide (4.0 g, 18.1 mmol). 1H NMR (DMSO-d6): δ 7.75 (s, 2H), 3.88 (s, 3H).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in diethyl ether/ethyl acetate
  3. washThe organic solution was washed with water, saturated sodium bicarbonate solution, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21825080c0784cec9a8e454ae7200668
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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