1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Methyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 2377795Notes

Reaction equation

HRID 2377795 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[CH3:26][O:27][C:28](=[O:43])[C:29]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)=[CH:30][C:31]([O:33]C)=O>CO>[F:42][C:39]1[CH:38]=[C:37]2[C:36](=[CH:41][CH:40]=1)[NH:35][C:29]([C:28]([O:27][CH3:26])=[O:43])=[CH:30][C:31]2=[O:33]

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 691174942-(4-Fluorophenylamino)but-2-enedioic Acid Dimethyl Ester

Product 1

HCID 11390401Methyl 6-fluoro-4-oxo-1,4-dihydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
235 °C

Procedure

250 ml de Dowtherm-A are brought to reflux (about 235° C.) under a nitrogen atmosphere. 41 g (0.16 M) of 2-(4-fluorophenylamino)but-2-enedioic acid dimethyl ester are then introduced dropwise. The methanol formed is separated out. Refluxing is maintained for 10 minutes after the end of introduction. The reaction mixture is then cooled to about 50° C., followed by addition of 250 ml of petroleum ether: a solid precipitates out. It is filtered off by suction, washed three times with petroleum ether and then dried under reduced pressure.

Workup

  1. customis separated out
  2. temperatureRefluxing
  3. temperatureis maintained for 10 minutes after the end of introduction
  4. temperatureThe reaction mixture is then cooled to about 50° C.
  5. additionfollowed by addition of 250 ml of petroleum ether
  6. customa solid precipitates out
  7. filtrationIt is filtered off by suction
  8. washwashed three times with petroleum ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7113174d69b9471faa06ebc43083603d
Source dataset
uspto-grants-2008_12
Patent number
US07470708B2

Reaction notes

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