Sulfuric Acid → HCID 2794448, compound

HRID 636072Notes

Reaction equation

HRID 636072 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.OS(O)(=O)=O.CCCCCC.C(OCC)(=O)C>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]2[C:4]=1[C:14]([CH3:15])=[CH:13][C:12](=[O:17])[NH:11]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 256077112854-83-8HCID 21226206Ethyl acetate hexane

Product 1

HCID 2794448HCID 2794448, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Compound 9 (13.9 g, 58.6 mmol) was taken in a 100 mL round bottom flask and cooled to 0° C. Conc. H2SO4 (35 mL, 657 mmol) was added dropwise for 10 min at 0° C. and allowed the reaction mixture to reach room temperature over a period of 30 min. After completion of the reaction (TLC hexane : ethyl acetate 1:1, Rf=0.3) it was poured into water (200 mL) and solid separated was filtered, the solid was washed with water till neutral to pH and dried under vacuum to give product 5,7-dimethoxy4-methyl-1,2-dihydro-2-quinolinone (11, 12.5 g) in 97.6% yield as a solid. M.P. 239-240° C.

Workup

  1. customseparated
  2. filtrationwas filtered
  3. washthe solid was washed with water till neutral
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8a6ec6bfd29445c78a6e7e48f7705527
Source dataset
uspto-grants-2001_02
Patent number
US06191279B1

Reaction notes

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