2-Methylquinoline → Quinoline Yellow

HRID 2292286Notes

Reaction equation

HRID 2292286 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].Cl[C:13]1[C:14](Cl)=[C:15](Cl)[C:16](Cl)=[C:17]2[C:22](=O)[O:21][C:19](=[O:20])[C:18]=12>OCC1CC2CC1C1C2CCC1.CO>[CH:8]1[CH:7]=[C:6]2[CH:5]=[CH:4][C:2]([CH:3]3[C:22](=[O:21])[C:17]4[C:18](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:19]3=[O:20])=[N:1][C:11]2=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 70602-MethylquinolineHCID 8326Tetrachlorophthalic anhydride

Product 1

HCID 6731Quinoline YellowYield 47.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 93698(Octahydro-1H-4,7-methanoinden-5-yl)methanolSolvent

Conditions

Temperature
190 °C

Procedure

4.3 g of quinaldine and 8.6 g of tetrachlorophthalic anhydride in 100 ml of 8-hydroxymethyltricyclo[5.2.1.02,6 ]decane [TCD alcohol M®, ex Hoechst] are stirred and heated under nitrogen to 190° C. in a 350 ml glass apparatus equipped with cooler, thermometer, gas inlet pipe and semi-anchor stirrer. The mixture is stirred for 4 hours at 190° C. and the resultant yellow suspension is cooled to 40° C., diluted with 150 ml of methanol and filtered. The filter cake is washed with methanol until colourless and the yellow pigment is dried at 80° C in a vacuum drying cabinet, affording 3.9 g of the yellow quinophthalone pigment of formula ##STR2## which is incorporated in powder form into printing inks and varnishes and gives strong, yellow colorations of good fastness properties.

Workup

  1. customequipped with cooler, thermometer, gas inlet pipe and semi-anchor stirrer
  2. temperaturethe resultant yellow suspension is cooled to 40° C.
  3. filtrationfiltered
  4. washThe filter cake is washed with methanol until colourless and the yellow pigment
  5. customis dried at 80° C in a vacuum
  6. customdrying cabinet

Sources & evidence

ORD record
ord-f6cba622a5d6479ebde1060968b1586a
Source dataset
uspto-grants-1989_01
Patent number
US04801702

Reaction notes

Loading…