2-Methylquinoline → HCID 621053, compound

HRID 1003349Notes

Reaction equation

HRID 1003349 reaction equation
[C:1]1([CH:9]=O)[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.C(OC(=O)C)(=O)C>C1(C)C(C)=CC=CC=1>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH:11]=[CH:9][C:1]1[CH:2]=[CH:3][C:4]([CH:7]=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 70602-MethylquinolineHCID 7918Acetic AnhydrideHCID 12173Terephthalaldehyde

Product 1

HCID 621053HCID 621053, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1,4-Benzenedialdehyde (30 g, 0.22 mol), 2-methylquinoline (21 g, 0.15 mol) and acetic anhydride (41.5 ml, 0.40 mol) were dissolved in 160 ml of xylene, followed by heating under reflux for 7 hours. After the reaction mixture was allowed to cool down to room temperature, 200 ml of petroleum ether were added and the resulting precipitate was collected by filtration. Further, the mother liquor was concentrated under reduced pressure and the residue was recrystallized from diethyl ether, whereby 13.6 g of the title compound were obtained (yield: 35%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 7 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. concentrationFurther, the mother liquor was concentrated under reduced pressure
  5. customthe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-bf1bed581af64984aba6621c42e7788e
Source dataset
uspto-grants-2000_04
Patent number
US06046212

Reaction notes

Loading…