Acetic Acid → Methyl 3-iodo-4-oxo-1,4-dihydroquinoline-6-carboxylate

HRID 533418Notes

Reaction equation

HRID 533418 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=[CH:3]1.C(O)(=O)C.[I:20]N1C(=O)CCC1=O>O>[I:20][C:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[NH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 16112715Methyl 4-hydroxyquinoline-6-carboxylate

Product 1

HCID 67773905Methyl 3-iodo-4-oxo-1,4-dihydroquinoline-6-carboxylateYield 111.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 4-oxo-1,4-dihydroquinoline-6-carboxylate (1.1 g) and acetic acid (30 mL) was added N-iodosuccinimide (1.1 g), followed by stirring at room temperature for one day. The reaction mixture was diluted with water, and the precipitate was collected by filtration to obtain methyl 3-iodo-4-oxo-1,4-dihydroquinoline-6-carboxylate (1.8 g).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5ce70bb9aed241c8bc8f1900aae8b498
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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