Sulfuric Acid → HCID 59398050, compound

HRID 2193089Notes

Reaction equation

HRID 2193089 reaction equation
S(=O)(=O)(O)O.C(O[CH:9]=[CH:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=[O:12])C>O>[CH3:25][O:24][C:22]1[CH:21]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[C:15]2[CH:9]=[CH:10][C:11](=[O:12])[NH:13][C:14]=2[CH:23]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67539207HCID 67539207, compound

Product 1

HCID 59398050HCID 59398050, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 mL of concentrated sulfuric acid cooled with ice, 1.86 g of methyl 3-((3-ethoxyacryloyl)amino)-5-methoxybenzoate was added little by little, and the mixture was stirred for 1 hour under cooling with ice. The reaction mixture was fed into water cooled with ice, the insoluble material was collected by filtration, and the insoluble material thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform:methanol=50:1] to obtain 346 mg of methyl 7-methoxy-2-oxo-1,2-dihydroquinoline-5-carboxylate.

Workup

  1. additionwas added little by little, and the mixture
  2. temperatureunder cooling with ice
  3. temperaturecooled with ice
  4. filtrationthe insoluble material was collected by filtration
  5. customthe insoluble material thus obtained
  6. customwas purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-8d1a6bdcc8aa4a9ba22d2ff5040c803e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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