Pyridine → HCID 131734643, compound

HRID 1771082Notes

Reaction equation

HRID 1771082 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][O+:7]([CH3:9])C.CO[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[O:19])[N:13]=1.N1C=CC=CC=1.F[B-](F)(F)F>C(Cl)Cl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:12][N:13]1[C:6]([O:7][CH3:9])=[CH:17][CH:16]=[CH:15][CH:14]1[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 26255Tetrafluoroborate2×HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 123253926-Methoxy-2-pyridinecarboxaldehyde

Product 1

HCID 131734643HCID 131734643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with trimethyloxonium tetrafluoroborate (198 mg, 1.33 mmol). The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with 2-methoxy-6-pyridinecarboxaldehyde (Aldrich #662933, 184 mg, 1.34 mmol) and was dissolved in CH2Cl2 (1.5 mL). The solution of pyridine was added via syringe onto the solid trimethoxonium tetrafluoroborate at room temperature. The vial which contained the pyridine was rinsed with CH2Cl2 (1 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. Over the course of the reaction (17 h), the solid trimethoxonium tetrafluoroborate gradually dissolved, the solution clarified, and an oil gradually formed. At the end of the reaction, hexanes (2 mL) were added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The solid or oil was then rinsed with several portions of hexanes followed by diethyl ether. Residual solvent was then removed in vacuo to provide the compound N-methyl-6-methoxy-2-pyridinecarboxaldehyde tetrafluoroborate. This oil was used for oxime formation without further purification.

Workup

  1. customThe vial was brought into a glove box
  2. customThe vial was sealed
  3. customremoved from the glove box
  4. washwas rinsed with CH2Cl2 (1 mL)
  5. customThe reaction
  6. customvial was kept at room temperature
  7. temperaturewas maintained at ca. 400-600 rpm
  8. customOver the course of the reaction (17 h)
  9. customan oil gradually formed
  10. additionwere added after which
  11. stirringstirring
  12. customthe solvent was removed by glass pipette
  13. washThe solid or oil was then rinsed with several portions of hexanes
  14. customResidual solvent was then removed in vacuo

Sources & evidence

ORD record
ord-443a1ff7e20444809e7919613380c135
Source dataset
uspto-grants-2016_02
Patent number
US09249100B2

Reaction notes

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