Diethyl Ether → Ethyl 8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1743290Notes

Reaction equation

HRID 1743290 reaction equation
C(O[C:4](=[O:22])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.CCCCCC.C(OCC)(=O)C.C(OCC)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:22])[C:18]2[C:13](=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 225911Diethyl 2-((2-nitrophenylamino)methylene)malonateHCID 21226206Ethyl acetate hexane

Product 1

HCID 734639Ethyl 8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
280 °C

Procedure

A solution of 2-[(2-Nitro-phenylamino)-methylene]-malonic acid diethyl ester (10 g, 32.44 mmol) dissolved in 20 ml of diphenyl ether in a 250 ml round bottom flask was heated and refluxed for 5 hrs at 280° C. with stirring. The reaction was monitered by TLC (n-hexane/ethyl acetate=3/1). After completing the reaction and cooling to room temperature, 200 ml of diethylether was added to the mixture and the resulting precipitate was collected by filtration, and the residue was washed with 200 ml of diethyl ether to give 8-Nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (6.5 g, 19.08 mmol, yield 59%).

Workup

  1. temperaturewas heated
  2. customthe reaction
  3. temperaturecooling to room temperature
  4. filtrationthe resulting precipitate was collected by filtration
  5. washthe residue was washed with 200 ml of diethyl ether

Sources & evidence

ORD record
ord-0de391c275584da8934b3927d273a173
Source dataset
uspto-grants-2006_03
Patent number
US07009053B2

Reaction notes

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