Anthracene-1,9-dicarboxylic acid → HCID 9830525, compound

HRID 1941262Notes

Reaction equation

HRID 1941262 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:16][CH:17]=[CH:18][C:5]=3[C:4](=[O:19])[N:3]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][NH2:29])[CH:8]=[C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]1=2.[C:30]1([C:47](O)=[O:48])[C:43]2[C:34](=[CH:35][C:36]3[C:41]([C:42]=2[C:44](O)=[O:45])=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[CH:16][CH:17]=[CH:18][C:5]=3[C:4](=[O:19])[N:3]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][N:29]1[C:47](=[O:48])[C:30]3[CH:31]=[CH:32][CH:33]=[C:34]4[C:43]=3[C:42](=[C:41]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]3=[CH:35]4)[C:44]1=[O:45])[CH:8]=[C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]1=2

Participants

4

Reactant 2

HCID 13155838Anthracene-1,9-dicarboxylic acidHCID 21460417HCID 21460417, compound

Product 1

HCID 9830525HCID 9830525, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1.0 g (2,5 mmol) of N-[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-N'-(2-aminoethyl)-1,3-propanediamine in 50 ml of toluene was treated with 0.62 g (2,5 mmol) of anthracene-1,9-dicarboxylic acid anhyride in 10 ml of toluene, refluxed for 6 hours, and cooled to room temperature. The solid was collected, dried in vacuo, and crystallized from toluene to give 0.8 g 48% of N,N'-Bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-1,3-propanediamine. M.p. 191° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe solid was collected
  3. customdried in vacuo
  4. customcrystallized from toluene

Sources & evidence

ORD record
ord-87a4dfde06114a73ba2498d26fa6192e
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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