Acetic Acid → HCID 69379745, compound

HRID 1181627Notes

Reaction equation

HRID 1181627 reaction equation
[C:1]1(=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=N)[NH:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=N)[NH:2]1.[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[CH2:23]1.[C:32]([OH:35])(=O)[CH3:33]>CN1C(=O)CCC1>[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[C:23]1=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[C:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3](=[C:33]3[C:32](=[O:35])[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22]3=[O:21])[NH:2]2)[NH:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 118151,3-IndandioneHCID 178508319HCID 178508319, compound

Product 1

HCID 69379745HCID 69379745, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

10.0 g of [1,1′]biisoindolylidene-3,3′-diimine and 16.9 g of 1,3-dioxoindane are stirred in a mixture of 100 ml of NMP and 100 ml of glacial acetic acid at reflux for 6 hours. After cooling to room temperature the suspension is filtered, the filter product is washed with a mixture of NMP and glacial acetic acid (1:1), subsequently ethanol and then water and dried at 60° C. This gives 10.8 g (54%) of a black powder of a compound of the following formula

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationis filtered
  3. washthe filter product is washed with a mixture of NMP and glacial acetic acid (1:1), subsequently ethanol
  4. dry with materialwater and dried at 60° C

Sources & evidence

ORD record
ord-872b1055f6514fcf9b87fd8a8c161375
Source dataset
uspto-grants-2007_10
Patent number
US07285663B2

Reaction notes

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