2-Methylquinoline → HCID 621053, compound

HRID 369423Notes

Reaction equation

HRID 369423 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. The resulting mixture was refluxed for 7 hours. After the mixture was allowed to cool down to room temperature, it was added to 200 ml of petroleum ether which had been warmed to 40-60° C. The resulting precipitate was filtered off. The mother liquor was concentrated and the crude product so obtained was recrystallized twice from etnanol, whereby 13.6 g of the title compound were obtained (yield: 35%).

Workup

  1. temperatureThe resulting mixture was refluxed for 7 hours
  2. temperaturehad been warmed to 40-60° C
  3. filtrationThe resulting precipitate was filtered off
  4. concentrationThe mother liquor was concentrated
  5. customthe crude product so obtained
  6. customwas recrystallized twice from etnanol

Sources & evidence

ORD record
ord-c60b79efdcfd4146ad45f9f902fe89ca
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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