1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 2741052, compound

HRID 2187603Notes

Reaction equation

HRID 2187603 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[CH:41][C:42]([O:44]C)=O)[C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:30]=1)([O-:28])=[O:27]>CCOCC.CO>[N+:26]([C:29]1[CH:30]=[C:31]2[C:32](=[CH:33][CH:34]=1)[NH:35][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:41][C:42]2=[O:44])([O-:28])=[O:27]

Participants

5

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 6052251,4-Dimethyl 2-[(4-nitrophenyl)amino]but-2-enedioate

Product 1

HCID 2741052HCID 2741052, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To Dowtherm A (trademark, 30 ml) refluxed under heating was added dimethyl 2-[(4-nitrophenyl)amino]-2-butenedioate (6.32 g, 22.6 mmol) obtained in Example 131, Step 1 over 5 min by small portions. The mixture was refluxed under heating for 25 min and the reaction mixture was cooled to room temperature. The reaction mixture was diluted with ether and the resulting precipitate was filtrated. The obtained crude crystals were suspended in methanol and collected by filtration to give methyl 1,4-dihydro-6-nitro-4-oxo-2-quinolinecarboxylate (4.75 g, 85%, dark brown crystals).

Workup

  1. temperatureunder heating
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 25 min
  4. filtrationthe resulting precipitate was filtrated
  5. customThe obtained crude crystals
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ed7d6abad22b49dea0d240e37ae08568
Source dataset
uspto-grants-2002_06
Patent number
US06410561B1

Reaction notes

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