1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178510310, compound

HRID 530213Notes

Reaction equation

HRID 530213 reaction equation
[C:1](/[C:3](=[CH:9]\[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)/[C:4]([O:6]CC)=O)#[N:2].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCCCCC>[OH:6][C:4]1[C:12]2[C:11](=[CH:16][CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=2)[N:10]=[CH:9][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 5943680HCID 5943680, compound

Product 1

HCID 178510310HCID 178510310, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-ethyl 2-cyano-3-((4-nitrophenyl)amino)acrylate (24.0 g) and Dowtherm A (500 mL) was added to a 1 L flask, the mixture was heated to reflux under nitrogen for 10 hours. After cooling to 50° C., the mixture was diluted with hexane (1 L). The product was filtered, washed with ethanol (100×2 mL), and dried to give 4-hydroxy-6-nitroquinoline-3-carbonitrile (Compound 16) as a brown solid (12.0 g).

Workup

  1. additionwas added to a 1 L flask
  2. temperaturethe mixture was heated
  3. temperatureto reflux under nitrogen for 10 hours
  4. filtrationThe product was filtered
  5. washwashed with ethanol (100×2 mL)
  6. customdried

Sources & evidence

ORD record
ord-b9bf4c68c8c6443ca165377f0645da44
Source dataset
uspto-grants-2016_05
Patent number
US09353062B2

Reaction notes

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