Biphenyl → 4-Hydroxyquinoline-6-carbonitrile

HRID 1699893Notes

Reaction equation

HRID 1699893 reaction equation
C1(C2C=CC=CC=2)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1.[C:26]([C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH:35]=[C:36]2[C:41](=[O:42])OC(C)(C)OC2=O)=[CH:30][CH:29]=1)#[N:27]>CCCCCC>[OH:42][C:41]1[C:30]2[C:31](=[CH:32][CH:33]=[C:28]([C:26]#[N:27])[CH:29]=2)[N:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 116947054-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

Product 1

HCID 116583514-Hydroxyquinoline-6-carbonitrileYield 90.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of biphenyl (10 ml) and diphenyl ether (30 ml) was heated at 250° C. and 5-(4-cyanophenylamino)methylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (3.28 g) was added thereto. The mixture was stirred for 1 hr. The reaction mixture was cooled to 80° C. while stirring and hexane (100 ml) was added. The mixture was stirred in an ice bath for 0.5 hr. The resulting solid was collected by filtration and washed with hexane to give the object compound (1.86 g) as a yellow-brown powder.

Workup

  1. temperatureThe reaction mixture was cooled to 80° C.
  2. stirringwhile stirring
  3. stirringThe mixture was stirred in an ice bath for 0.5 hr
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with hexane

Sources & evidence

ORD record
ord-eb4e478025e747f0bf065ddb1a5809e9
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

Loading…