Potassium Carbonate → HCID 15917391, compound

HRID 1758142Notes

Reaction equation

HRID 1758142 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1>C(C(C)=O)C>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 15917392HCID 15917392, compound

Product 1

HCID 15917391HCID 15917391, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

After heating at reflux a mixture of 1.5 grams (0.0067 mole) 2-(5-chloropyrimidin-2-yloxy)phenol, 1.2 grams potassium carbonate, 1.3 grams 2-chloro-5-nitropyridine and 40 ml of methyl ethyl ketone, the reaction mixture was poured into excess H2 0 and the aqueous mixture extracted with ethyl ether (200 ml). The ether layer was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and evaporated to yield 2.3 grams of a yellow-orange oil which was purified by silica gel column chromatography (CH2Cl2 as the eluent). NMR (CDCl3): δ6.90 (d, 1H, pyridine ring proton), 7.35 (s, 4H, ArH), 8.25-8.50 (m, 1H, pyridine ring proton), 8.45 (s, 2H, pyrimidine ring protons), 8.95 (d, 1H, pyridine ring proton).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux
  3. additionthe reaction mixture was poured into excess H2 0
  4. extractionthe aqueous mixture extracted with ethyl ether (200 ml)
  5. washThe ether layer was washed with saturated NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-81063725072944429c8078058b7b7030
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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