1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → 4-Hydroxyquinoline-6-carbonitrile

HRID 1437387Notes

Reaction equation

HRID 1437387 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)C(=O)O1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCOCC>[O:8]=[C:6]1[C:12]2[C:11](=[CH:18][CH:17]=[C:14]([C:15]#[N:16])[CH:13]=2)[NH:10][CH:9]=[CH:5]1

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 116947054-(((2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzonitrile

Product 1

HCID 116583514-Hydroxyquinoline-6-carbonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzonitrile (a) (27.5 g) was added portionwise over 5 minutes to refluxing Dowtherm A (200 ml). After refluxing an additional 5 minutes, the mixture was allowed to cool to room temperature and diluted with ether (200 ml) with stirring. The product was filtered off, washed thoroughly with ether and air dried to provide a gold solid (16.2 g, 94%).

Workup

  1. temperatureAfter refluxing an additional 5 minutes
  2. filtrationThe product was filtered off
  3. washwashed thoroughly with ether and air
  4. customdried

Sources & evidence

ORD record
ord-3be0c4741a29485f881d876f25db75a7
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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