Biphenyl → 1,4-Dihydro-5-methyl-8-nitro-4-oxoquinoline

HRID 613563Notes

Reaction equation

HRID 613563 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1.[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([N+:45]([O-:47])=[O:46])=[C:31]([CH:44]=1)[NH:32][CH:33]=[C:34]1[C:42](=[O:43])OC(C)(C)OC1=O>CCCCCC>[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([N+:45]([O-:47])=[O:46])=[C:31]2[C:44]=1[C:42](=[O:43])[CH:34]=[CH:33][NH:32]2

Participants

5

Reactant 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 53705573Isopropylidene (5-methyl-2-nitroanilino)methylenemalonate

Product 1

HCID 195926861,4-Dihydro-5-methyl-8-nitro-4-oxoquinolineYield 90.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of diphenyl ether (37 g) and biphenyl (13 g) was added isopropylidene (5-methyl-2-nitroanilino)methylenemalonate (14.6 g) at 220° C., and the mixture was heated at the same temperature for half an hour. The reaction mixture was allowed to cool to 100° C. and then n-hexane (100 ml) was added dropwise to the mixture. After cooling to ambient temperature, the precipitate was collected by filtration. The solid was washed with hot ethanol (70 ml) and allowed to cool to ambient temperature. The solid was collected by filtration and air-dried to give 1,4-dihydro-5-methyl-8-nitro-4-oxoquinoline (8.8 g) as a dark brown solid.

Workup

  1. temperaturethe mixture was heated at the same temperature for half an hour
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe precipitate was collected by filtration
  4. washThe solid was washed with hot ethanol (70 ml)
  5. temperatureto cool to ambient temperature
  6. filtrationThe solid was collected by filtration
  7. customair-dried

Sources & evidence

ORD record
ord-8ac6ca2330e742f1989c43af8538ad46
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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