Ammonia → HCID 12051826, compound

HRID 2228604Notes

Reaction equation

HRID 2228604 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH:2]=1.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.[CH3:21][C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25].[NH3:28]>CCO>[C:22]([C:23]1[C:24]([CH3:25])=[C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)[NH:28][C:19]=1[C:16]1[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=1)(=[O:27])[CH3:21]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 133894-PyridinecarboxaldehydeHCID 31261AcetylacetoneHCID 780724-Quinolinecarboxaldehyde

Product 1

HCID 12051826HCID 12051826, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-quinolinecarboxaldehyde (2.3 g; 14.8 mmol), 4-pyridinecarboxaldehyde (1.6 g ; 14.8 mmol) in EtOH (40 mL) was added 2,4-pentanedione (2 g; 20 mmol) and 25% aqueous ammonia solution (8 ml) at room temperature. The mixture was heated at reflux temperature for 18 hours. After cooling, volatiles were removed by evaporation. Chromatographic purification of the residue on silica gel eluting with CH2Cl2—EtOH (20:1→8:1) provided 1.1 g, which was recrystallized from EtOH to afford the title compound (0.82 g, 17% yield) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 18 hours
  3. temperatureAfter cooling
  4. customvolatiles were removed by evaporation
  5. customChromatographic purification of the residue on silica gel eluting with CH2Cl2—EtOH (20:1→8:1)
  6. customprovided 1.1 g, which
  7. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-514bd19bad5b465ba786a94e26d96f07
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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