Piperidine → N-phenyl beta-(8-hydroxy-5-quinolyl)-alpha-cyanoacrylamide

HRID 266700Notes

Reaction equation

HRID 266700 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=O)=[CH:4][CH:3]=1.[C:14]1([NH:20][C:21](=[O:25])[CH2:22][C:23]#[N:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1>C(O)C>[C:14]1([NH:20][C:21](=[O:25])[C:22]([C:23]#[N:24])=[CH:12][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[C:11]3[C:6]=2[CH:7]=[CH:8][CH:9]=[N:10]3)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 69296Acetamide, 2-cyano-N-phenyl-HCID 2753638-Hydroxyquinoline-5-carbaldehyde

Product 1

HCID 54517088N-phenyl beta-(8-hydroxy-5-quinolyl)-alpha-cyanoacrylamideYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 8-hydroxy-5-quinolinecarboxaldehyde (1.732 g, 0.010 mol), N-phenyl cyanoacetamide (1.602 g, 0.010 mol) and piperidine (0.255 g, 0.003 mol) in absolute ethanol (50 ml) was heated for 3 h at reflux. The reaction mixture was chilled to about 10°-15° C., the precipitate filtered, the residue washed with ice-cooled ethanol and dried under vacuum. Almost pure title compound was obtained in about 75% yield (2.365 g).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture was chilled to about 10°-15° C.
  3. filtrationthe precipitate filtered
  4. washthe residue washed with ice-
  5. temperaturecooled ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ca1bb5d3581b40c3be74bfd295d6c6c7
Source dataset
uspto-grants-1997_07
Patent number
US05652250

Reaction notes

Loading…