Acetic Acid → HCID 86627515, compound

HRID 1970055Notes

Reaction equation

HRID 1970055 reaction equation
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[CH2:15]([C:17]([O-:19])=[O:18])[CH3:16].C(O)(=O)C.[I:24]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:24][C:7]1[CH:6]=[CH:5][C:4]2[NH:3][C:2](=[O:1])[C:11]3[NH:12][CH:13]=[CH:14][C:10]=3[C:9]=2[CH:8]=1.[CH2:15]([C:17]([O-:19])=[O:18])[CH3:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 807IodineHCID 86627461HCID 86627461, compound

Product 1

HCID 86627515HCID 86627515, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

1.49 g (4.7 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid is added to a suspension of 1.61 g (5.17 mmol) of diiodine and 1.31 g (5.17 mmol) of silver sulfate in anhydrous ethanol (100 mL). The reaction mixture is stirred at room temperature for 6 hours then the solvents are evaporated under vacuum. The residue is taken up in water and the product is extracted copiously with a mixture of ethyl acetate/methanol 95/5. The organic phases are dried over magnesium sulfate, filtered on celite and evaporated under vacuum to give 1.4 g (78%) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customthe solvents are evaporated under vacuum
  2. extractionthe product is extracted copiously with a mixture of ethyl acetate/methanol 95/5
  3. dry with materialThe organic phases are dried over magnesium sulfate
  4. filtrationfiltered on celite
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-119c4cd400f6482985c2f2586f555758
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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