Acetic Anhydride → HCID 178423899, compound

HRID 2105095Notes

Reaction equation

HRID 2105095 reaction equation
[I-].[N+:2]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[CH2:8][N+:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH3:19])([CH3:18])[C:10]=1[CH3:20])([O-:4])=[O:3].O[C:28]1[C:29](=[O:34])[C:30](=O)[C:31]=1[OH:32].[I-].[C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][N+:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]([CH3:54])([CH3:53])[C:45]=1[CH3:55])([OH:38])=[O:37].C(OC(=O)C)(=O)C>C(O)(=O)C.N1C=CC=CC=1>[C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][N:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]([CH3:53])([CH3:54])[C:45]1=[CH:55][C+:28]1[C:31]([O-:32])=[C:30]([CH:20]=[C:10]2[C:11]([CH3:19])([CH3:18])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]2[CH2:8][C:7]2[CH:6]=[C:5]([N+:2]([O-:4])=[O:3])[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=2)[C+:29]1[O-:34])([OH:38])=[O:37]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 17913Squaric acidHCID 179021401-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodideHCID 685338171-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium iodide

Product 1

HCID 178423899HCID 178423899, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

To 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide (467 mg) was added 3,4-dihydroxy-3-cyclobuten-1,2-dione (110 mg), 1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium iodide (354 mg), pyridine (4.5 ml), acetic acid (4.5 ml) and acetic anhydride (1 ml). The mixture was heated to reflux for 3 hours and the solvent then stripped using rotary evaporation. This crude material was subjected to silica flash column chromatography (eluted with MeOH/DCM). Fractions containing product were combined and stripped of solvent. The resulting material was further purified by reverse phase HPLC (CH3CN/H2O/TFA).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customevaporation
  4. washThis crude material was subjected to silica flash column chromatography (eluted with MeOH/DCM)
  5. additionFractions containing product
  6. customThe resulting material was further purified by reverse phase HPLC (CH3CN/H2O/TFA)

Sources & evidence

ORD record
ord-fb931656e7474c99a00cb47b820d5fb4
Source dataset
uspto-grants-2009_08
Patent number
US07579140B2

Reaction notes

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