Potassium Carbonate → 2,6-Dichloro-4-methoxypyridine

HRID 594090Notes

Reaction equation

HRID 594090 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Cl:11])[N:3]=1.[C:12](=O)([O-])[O-:13].[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:13][CH3:12])[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 38410702,6-Dichloro-4-nitropyridine

Product 1

HCID 33199932,6-Dichloro-4-methoxypyridineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 2,6-dichloro-4-nitropyridine (1.0 equiv.), potassium carbonate (3 equiv.) and methanol (20 equiv.) were heated to 70° C. for 25 min in the microwave. The reaction mixture was diluted with methanol and was decanted from remaining solids. After concentration, the mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give 2,6-dichloro-4-methoxypyridine in 88% yield. LCMS (m/z) (M+H)=177.9/179.9, Rt=0.72 min.

Workup

  1. customwas decanted
  2. concentrationAfter concentration
  3. customthe mixture was partitioned between water and EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated
  7. customdried under vacuo

Sources & evidence

ORD record
ord-6c7a5f9a523a4876b4d4c9633ffa9243
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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