Hydrochloric Acid → 6,7-Dimethoxyquinolin-4(3H)-one

HRID 1375157Notes

Reaction equation

HRID 1375157 reaction equation
C[O-].[Na+].[CH3:4][C:5]([C:7]1[C:12]([NH2:13])=[CH:11][C:10]([O:14][CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)=[O:6].[CH:18](OCC)=O.Cl>O.O1CCCC1>[CH3:17][O:16][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[O:14][CH3:15])[N:13]=[CH:18][CH2:4][C:5]2=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-HCID 10942334Sodium Methoxide

Product 1

HCID 224782456,7-Dimethoxyquinolin-4(3H)-oneYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Tetrahydrofuran (THF) (5.3 L) and sodium methoxide (313 g) were added to 2-amino-4,5-dimethoxyacetophenone (337 g), and the mixture was stirred at 20° C. for 30 min. Ethyl formate (858 g) was added to the reaction solution at 0° C., and the mixture was stirred at 20° C. for one hr. Water (480 mL) was added thereto at 0° C., and the mixture was neutralized with 1 N hydrochloric acid. The resultant precipitate was collected by filtration, and the filtered product was slurried in water (2 L) for washing. The slurry was filtered, and the filtered product was then dried under the reduced pressure to give 6,7-dimethoxy-4-quinolone (352 g, yield 81.50%).

Workup

  1. stirringthe mixture was stirred at 20° C. for one hr
  2. customat 0° C.
  3. filtrationThe resultant precipitate was collected by filtration
  4. washfor washing
  5. filtrationThe slurry was filtered
  6. customthe filtered product was then dried under the reduced pressure

Sources & evidence

ORD record
ord-286967dc26a54d948c9d8e16c9603f2d
Source dataset
uspto-grants-2007_01
Patent number
US07166722B2

Reaction notes

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