Chloranil → HCID 178516979, compound

HRID 926659Notes

Reaction equation

HRID 926659 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:19]3[C:11](=[CH:12][C:13]4[CH:14]([C:21]5[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=5)[C:15](=[O:20])[NH:16][C:17]=4[CH:18]=3)[NH:10][C:9]2=[O:28])=[CH:4][CH:3]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(=O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([C:14]2[C:15](=[O:20])[NH:16][C:17]3[C:13]=2[CH:12]=[C:11]2[C:19](=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)[C:9](=[O:28])[NH:10]2)[CH:18]=3)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 666549393,7-Bis-(4-bromo-phenyl)-5,7-dihydro-1H,3H-pyrrolo[2,3-f]indole-2,6-dione

Product 1

HCID 178516979HCID 178516979, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

3,7-Bis-(4-bromo-phenyl)-5,7-dihydro-1H,3H-pyrrolo[2,3-f]indole-2,6-dione (7.250 g, 14.55 mmol) (1.2) was dissolved into acetic acid (215 cm3), chloranil (7.157 g, 29.11 mmol) is added and the reaction mixture heated to 50° C. for 16 hours. After cooling down, the resulting precipitate is filtered and washed with acetic acid. The recovered solid is purified by trituration with nitrobenzene (120 cm3) at 200° C. followed by trituration with diethyl ether (100 cm3) to obtain the pure product (4.512 g, Yield: 63%). NMR (1H, 300 MHz, DMSO): δ 10.37 (br, 2H), 7.71 (d, J=8.7 Hz, 4H), 7.61 (d, J=8.7 Hz, 4H), 6.34 (s, 2H).

Workup

  1. additionis added
  2. temperatureAfter cooling down
  3. filtrationthe resulting precipitate is filtered
  4. washwashed with acetic acid
  5. customThe recovered solid is purified by trituration with nitrobenzene (120 cm3) at 200° C.

Sources & evidence

ORD record
ord-31196ffcb01443799f52a990525057c1
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Reaction notes

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