2,6-Dimethylphenol → 2-(2,6-Dimethylphenoxy)-5-nitropyridine

HRID 1505333Notes

Reaction equation

HRID 1505333 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[OH:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[O:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 126759562-(2,6-Dimethylphenoxy)-5-nitropyridineYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In a 20 mL microwave vial 2-chloro-5-nitropyridine (500 mg, 3.15 mmol) was dissolved in N,N-dimethylformamide (10 mL) to give a pale yellow solution. 2,6-dimethylphenol (385 mg, 3.15 mmol) and potassium carbonate (1308 mg, 9.46 mmol) were added. The reaction vessel was sealed and heated under microwave irradiation (Biotage instrument) at 110° C. for 1 hour. The reaction mixture was quenched with 10 mL of water and diluted with 10 mL of Et2O. Phases were separated through a separating funnel. The organic phase was washed with 3 times 10 mL of water, 10 mL of brine, dried over sodium sulphate, filtered and evaporated under vacuum to afford the title compound as a pale orange oil (555.9 mg).

Workup

  1. customto give a pale yellow solution
  2. customThe reaction vessel was sealed
  3. customThe reaction mixture was quenched with 10 mL of water
  4. additiondiluted with 10 mL of Et2O
  5. customPhases were separated through a separating funnel
  6. washThe organic phase was washed with 3 times 10 mL of water, 10 mL of brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-046f1bb01bce407396cb36c81158de40
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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