HCID 22503303, compound → HCID 22503325, compound

HRID 1814485Notes

Reaction equation

HRID 1814485 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:14][C:13](=O)[C:12]3[N:16]=[CH:17][CH:18]=[CH:19][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1>P(Cl)(Cl)(Cl)=O>[C:13]([C:12]1[C:11]([C:10]#[C:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:19][CH:18]=[CH:17][N:16]=1)#[N:14]

Participants

3

Reactant 1

HCID 22503303HCID 22503303, compound

Product 1

HCID 22503325HCID 22503325, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (20 ml) was added to 6-(4-methoxyphenyl)-7,8-dihydropyrido[2,3-c]pyridin-8-one (0.70 g, 2.77 mmol), and the mixture was heated under reflux for 1.5 hr. After cooling as it was, excess phosphorus oxychloride was evaporated. To the resulting residue was added N-ethylpiperazine (35 ml), and the mixture was stirred in nitrogen atmosphere at 100° C. for 2 hr. After cooling as it was, the reaction solution was evaporated. The resulting residue was dissolved in ethyl acetate, washed sequentially with a 10% aqueous solution of sodium carbonate, water and brine, and dried over magnesium sulfate. Then, the solvent was evaporated, and the resulting residue was purified by NH-silica gel column chromatography (n-hexene/ethyl acetate system), to give the title compound as pale brown crystals (0.98 g, yield; quantitative).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureAfter cooling as it
  4. customexcess phosphorus oxychloride was evaporated
  5. additionTo the resulting residue was added N-ethylpiperazine (35 ml)
  6. temperatureAfter cooling as it
  7. customthe reaction solution was evaporated
  8. dissolutionThe resulting residue was dissolved in ethyl acetate
  9. washwashed sequentially with a 10% aqueous solution of sodium carbonate, water and brine
  10. dry with materialdried over magnesium sulfate
  11. customThen, the solvent was evaporated
  12. customthe resulting residue was purified by NH-silica gel column chromatography (n-hexene/ethyl acetate system)

Sources & evidence

ORD record
ord-07cf560519cd4db89d4e4b9c01ad4426
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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