2-Methylquinoline → 7251-91-4

HRID 579729Notes

Reaction equation

HRID 579729 reaction equation
C(OC(=O)C)(=O)C.[N:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:9]=1[CH3:10].[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20]>O>[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)/[CH:25]=[CH:10]/[C:9]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 70602-MethylquinolineHCID 74493-NitrobenzaldehydeHCID 7918Acetic Anhydride

Product 1

HCID 53766177251-91-4Yield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To 3.1 g of acetic anhydride, 7.2 g of quinaldine and 7.6 g of m-nitrobenzaldehyde were added and the resulting mixture was stirred under nitrogen atmosphere at 160° C. for 4 hours. After completion of the reaction, water was added to the reaction mixture and the resulting solid was collected by filtration and dried. Recrystallization from toluene gave 12.1 g (yield: 88%) of the captioned compound as an yellow powder.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationthe resulting solid was collected by filtration
  3. customdried
  4. customRecrystallization from toluene

Sources & evidence

ORD record
ord-6805216384184842b8c78adcbe30a236
Source dataset
uspto-grants-1988_06
Patent number
US04749701

Reaction notes

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