Ethanolamine → HCID 650462, compound

HRID 649609Notes

Reaction equation

HRID 649609 reaction equation
Cl[C:2]1[C:3](=[O:20])[NH:4][C:5]2[CH:19]=[CH:18][CH:17]=[C:7]3[C:8](=[O:16])[C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[C:11]=1[C:6]=23.[CH2:21]([CH2:23][NH2:24])[OH:22].[C:25]([O-])(=O)C.[Na+]>CO>[OH:22][CH2:21][CH2:23][NH:24][C:2]1[C:3](=[O:20])[N:4]([CH3:25])[C:5]2[CH:19]=[CH:18][CH:17]=[C:7]3[C:8](=[O:16])[C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[C:11]=1[C:6]=23

Participants

5

Reactant 3

HCID 700EthanolamineHCID 517045Sodium AcetateHCID 20141868HCID 20141868, compound

Product 1

HCID 650462HCID 650462, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-chloro-3H-dibenz[f,ij]isoquinoline-2,7-dione (1.8 g), ethanolamine (14 ml), sodium acetate (1 g), and a trace of cupric acetate was heated at 100°-110° C. until reaction appeared to be complete (~1 hr). After cooling, methanol (10 ml) was added to the reaction mixture at about 80° C. Upon further cooling the product crystallized in the form of yellow solid. After being isolated by filtration and recrystallized from methyl Cellosolve, the product melted at 203°-206° C. and had an absorption maxium at 441 nm in the visible spectrum in acetone solution, thus imparting a greenish-yellow color thereto. The structure is as follows: ##STR5##

Workup

  1. custom(~1 hr)
  2. temperatureAfter cooling
  3. temperatureUpon further cooling the product
  4. customcrystallized in the form of yellow solid
  5. customAfter being isolated by filtration
  6. customrecrystallized from methyl Cellosolve

Sources & evidence

ORD record
ord-2ce56b99a38b49f19d3229731a5f5036
Source dataset
uspto-grants-1988_04
Patent number
US04740581

Reaction notes

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