Biphenyl → HCID 178436852, compound

HRID 726277Notes

Reaction equation

HRID 726277 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1.[CH3:26][O:27][C:28]1[CH:43]=[CH:42][CH:41]=[CH:40][C:29]=1[NH:30][C:31]([CH2:38][CH3:39])=[CH:32][C:33]([O:35]CC)=O>CCCCCC>[CH2:38]([C:31]1[CH:32]=[C:33]([OH:35])[C:40]2[C:29](=[C:28]([O:27][CH3:26])[CH:43]=[CH:42][CH:41]=2)[N:30]=1)[CH3:39]

Participants

5

Reactant 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 70181045HCID 70181045, compound

Product 1

HCID 178436852HCID 178436852, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
235 °C

Procedure

To a mixture of diphenyl ether (30 ml) and biphenyl (30 g) was added ethyl 3-(2-methoxyanilino)-2-pentenoate (15.1 g) during which time the internal temperature was maintained 230°-235° C. The mixture was stirred at 235° C. for 1 hour. To the reaction mixture was added hexane (150 ml). The precipitate was collected by vacuum filtration and washed with hexane to give 2-ethyl-4-hydroxy-8-methoxyquinoline (10.37 g) as crystals.

Workup

  1. temperaturewas maintained 230°-235° C
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-947c99e09bea48b782ba8c9fad1a3244
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

Loading…