3,5-Dichloro-2-cyanopyridine → 3-Chloro-5-methoxypicolinonitrile

HRID 1003398Notes

Reaction equation

HRID 1003398 reaction equation
[C:1]([C:3]1[C:8]([Cl:9])=[CH:7][C:6](Cl)=[CH:5][N:4]=1)#[N:2].[CH3:11][O-:12].[Na+]>C1COCC1>[Cl:9][C:8]1[C:3]([C:1]#[N:2])=[N:4][CH:5]=[C:6]([O:12][CH3:11])[CH:7]=1

Participants

4

Reactant 2

HCID 27696993,5-Dichloro-2-cyanopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 187968643-Chloro-5-methoxypicolinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 27A (0.865 g, 5.0 mmol) was dissolved in THF (10 mL) and 0.27 g NaOMe was added. After 3 h and 25° C., the reaction was quenched in 5% aq. NaHCO3 solution and extracted with diethyl ether. The organic phase was dried, evaporated, and the residue purified by column chromatography, eluting with 70:30 hexanes:ethyl acetate to yield 0.27 g (32%, second eluting component) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.95 (s, 3H), 7.29 (d, 1H), 8.28 (d, 1H).

Workup

  1. custom25° C., the reaction was quenched in 5% aq. NaHCO3 solution
  2. extractionextracted with diethyl ether
  3. customThe organic phase was dried
  4. customevaporated
  5. customthe residue purified by column chromatography
  6. washeluting with 70:30 hexanes

Sources & evidence

ORD record
ord-b3b2272e662046c5b73eb0555649b0f7
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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