1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → 6,7-Dimethoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile

HRID 1934918Notes

Reaction equation

HRID 1934918 reaction equation
[C:1]([C:3](=[CH:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[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>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH3:20])[NH:10][CH:9]=[C:3]([C:1]#[N:2])[C:4]2=[O:6]

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 691625702-Cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl ester

Product 1

HCID 111838146,7-Dimethoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 40 g of ethyl 2-cyano-3-(3,4-dimethoxyphenylamino)acrylate and 1.2 L of Dowtherm® A was refluxed for 10 h, cooled, and diluted with hexane. The resulting solid was filtered, washed with hexane followed by dichloromethane, and dried; mp 330-350° C. (dec).

Workup

  1. temperatureA was refluxed for 10 h
  2. temperaturecooled
  3. filtrationThe resulting solid was filtered
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-2590f1de15aa4810b32e93fb65b02ad5
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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