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

HRID 1782005Notes

Reaction equation

HRID 1782005 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

Intermediate (a) (27.5 g, 0.101 mol) was slowly added over five minutes to refluxing Dowtherm A (200 ml). After an additional five minutes at reflux, the mixture was allow to cool to room temperature then ether (200 ml) was added. The product was filtered off, thoroughly washed with ether then air dried to afford the product as a gold coloured solid (16.2 g, 94%).

Workup

  1. temperatureAfter an additional five minutes at reflux
  2. filtrationThe product was filtered off
  3. washthoroughly washed with ether
  4. customair dried

Sources & evidence

ORD record
ord-0e707d5fa7344215a30237ad995c66c0
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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