Sodium Bicarbonate → 8-Nitroquinolin-2(1H)-one

HRID 2306254Notes

Reaction equation

HRID 2306254 reaction equation
C([NH:4][C:5]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:6]=1[CH:7]=[CH:8][C:9](OC)=[O:10])(=O)C.C([O-])(O)=O.[Na+]>Cl>[N+:17]([C:16]1[CH:15]=[CH:14][CH:13]=[C:6]2[C:5]=1[NH:4][C:9](=[O:10])[CH:8]=[CH:7]2)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 70171492Methyl 2-acetamido-3-nitrocinnamate

Product 1

HCID 3465208-Nitroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 2-acetamido-3-nitrocinnamate, as described above in Step B, (5.76 g, 21.8 mmol) was dissolved in 3 N aqueous HCl (220 mL) and the solution was heated at reflux for 72 hours, cooled, neutralized with NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 72 hours
  3. temperaturecooled
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8f29881f4a041aea23c6dec57606354
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

Loading…