Perchloric Acid → 4-Hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

HRID 908554Notes

Reaction equation

HRID 908554 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]([O:17]C(C)(C)C)=[O:16].Cl(O)(=O)(=O)=O>C(#N)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 59340042tert-Butyl 4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 593400774-Hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (4.1 g, 10 mmol) and Acetonitrile (20 ml), cooled in an ice bath, was added 70% perchloric acid (0.2 ml) and the mixture was stirred 30 sec. A yellow solid was filtered. Yield=0.5 g.

Workup

  1. filtrationA yellow solid was filtered

Sources & evidence

ORD record
ord-96ed0660bb1d44839166a32ad7808d49
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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