2-Ethylphenol → HCID 40541027, compound

HRID 1505336Notes

Reaction equation

HRID 1505336 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH3:12]

Participants

5

Reactant 3

HCID 69972-EthylphenolHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 40541027HCID 40541027, compound

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 light brown solution. 2-ethylphenol (0.378 mL, 3.15 mmol) and K2CO3 (1308 mg, 9.46 mmol) were added. The reaction vessel was sealed and heated in Biotage Initiator at 110° C. for 1 hour. After cooling the reaction was complete. 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 3×10 mL of water, 10 mL of brine, dried over sodium sulphate, filtered and evaporated under vacuum to give the title compound as a pale orange oil. (623 mg).

Workup

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

Sources & evidence

ORD record
ord-6a0b770e6b4d4af6b663fbb8e81839ea
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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