Phosphorus oxychloride → HCID 67026592, compound

HRID 2113419Notes

Reaction equation

HRID 2113419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:10])=[N+:4]([O-])[C:3]=1[C:12]([O:14][CH3:15])=[O:13].P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[N:4][C:5]([CH2:8][O:9][CH3:10])=[CH:6][C:7]=1[Cl:18]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67026601HCID 67026601, compound

Product 1

HCID 67026592HCID 67026592, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-chloro-6-(methoxymethyl)pyridine-2-carboxylate 1-oxide (1.64 g, 7.08 mmol) in acetonitrile (28 mL) was added phosphorus oxychloride (1.32 mL, 14.16 mmol) and the mixture stirred at reflux for 4 hours. After cooling to room temperature the mixture was concentrated to dryness in vacuo. The residue was diluted with ethyl ether and carefully washed with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with ethyl ether. After the organic layers were combined, the solution was dried (MgSO4), filtered and concentrated to dryness to give crude methyl 3,4-dichloro-6-(methoxymethyl)pyridine-2-carboxylate (1.74 g) as a yellow oil; 1H NMR (CDCl3): δ 7.70 (s, 1H), 4.60 (s, 2H), 4.00 (s, 3H), 3.40 (s, 3H).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationwas concentrated to dryness in vacuo
  3. additionThe residue was diluted with ethyl ether
  4. washcarefully washed with saturated NaHCO3 solution
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl ether
  7. dry with materialthe solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-29d0577805284546844721aea4106edc
Source dataset
uspto-grants-2008_10
Patent number
US07432227B2

Reaction notes

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