Tetrachlorophthalic anhydride → HCID 15451104, compound

HRID 634911Notes

Reaction equation

HRID 634911 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[C:6]([CH3:14])=[CH:5][C:4]1([CH3:16])[CH3:15])[CH3:2].[Cl:17][C:18]1[C:19]([Cl:31])=[C:20]([Cl:30])[C:21]([Cl:29])=[C:22]2[C:27](=[O:28])[O:26][C:24](=[O:25])[C:23]=12>ClCCCl>[C:27]([C:22]1[C:21]([Cl:29])=[C:20]([Cl:30])[C:19]([Cl:31])=[C:18]([Cl:17])[C:23]=1[C:24]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[OH:13])[N:3]([CH2:1][CH3:2])[C:4]([CH3:15])([CH3:16])[CH:5]=[C:6]2[CH3:14])=[O:25])([OH:28])=[O:26]

Participants

4

Reactant 2

HCID 8326Tetrachlorophthalic anhydrideHCID 154511031-Ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-ol

Product 1

HCID 15451104HCID 15451104, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

24 g (0.11 mol) N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline and 31.6 g (0.11 mol) tetrachloro-phthalic acid anhydride were dissolved in 200 ml 1,2-dichloroethane and refluxed for 3 h. After cooling, the solution was filtered and evaporated to dryness in a rotary evaporator. The residue was suspended in ca. 500 ml chloroform and heated to boiling. The solid (=product) was filtered. In order to increase the yield, the mother liquor was rotary evaporated to dryness and purified by column chromatography. For this ca. 100 g silica gel (ICN silica 32-63, 60A) was used as a separation material for ca. 3 g crude product. A mixture of chloroform +5% ethanol serve as a flow agent. The filtered solid was dissolved in ca. 1 l diethyl ether. After filtering the solvent was removed by distillation and the residue was dried to form a yellow solid.

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureAfter cooling
  3. filtrationthe solution was filtered
  4. customevaporated to dryness in a rotary evaporator
  5. temperatureheated to boiling
  6. filtrationThe solid (=product) was filtered
  7. temperatureIn order to increase the yield
  8. customthe mother liquor was rotary evaporated to dryness
  9. custompurified by column chromatography
  10. additionA mixture of chloroform +5% ethanol
  11. dissolutionThe filtered solid was dissolved in ca. 1 l diethyl ether
  12. filtrationAfter filtering the solvent
  13. customwas removed by distillation
  14. customthe residue was dried
  15. customto form a yellow solid

Sources & evidence

ORD record
ord-f4d97ebaa59e45d5a8cf2cc55f05fc8b
Source dataset
uspto-grants-2001_02
Patent number
US06184379B2

Reaction notes

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