Sulfuric Acid → HCID 59398050, compound

HRID 39717Notes

Reaction equation

HRID 39717 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-bd2a256a8434497eb81b7af1ed60fa10
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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