2-Hydroxyquinoline → 3,4,6-trichlorophthalic Acid

HRID 1742091Notes

Reaction equation

HRID 1742091 reaction equation
FC1C=C(F)C(F)=CC=1C(O)=[O:5].N1C2C(=CC=CC=2)C=CC1=O.[Cl:24][C:25]1[C:26](Cl)=[C:27]([Cl:37])[C:28]([Cl:36])=[C:29]2[C:34](=[O:35])[O:33][C:31](=[O:32])[C:30]=12>[OH-].[Na+].[Zn]>[Cl:36][C:28]1[C:27]([Cl:37])=[CH:26][C:25]([Cl:24])=[C:30]([C:31]([OH:32])=[O:5])[C:29]=1[C:34]([OH:33])=[O:35]

Participants

5

Reactant 3

HCID 60382-HydroxyquinolineHCID 8326Tetrachlorophthalic anhydride2×HCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 111191343,4,6-trichlorophthalic Acid

Reagents, catalysts & solvents 1

HCID 86748067NaOH ZnSolvent

Procedure

2,4,5-Trifluorobenzoic acid (2,4,5--TiFBA) is used as an intermediate in preparing quinolone antibacterials. It is prepared by a process that begins with tetrachlorophthalic anhydride. Tetrachlorophthalic anhydride is first hydrodechlorinated in NaOH/Zn to produce 3,4,6-trichlorophthalic acid, followed by imidization using methylamine to form 3,4,6-trichloro-N-methylphthalimide. That product is fluorinated by KF to form 3,4,6-trifluoro-N-methyl phthalimide, which is hydrolyzed to produce 3,4,6-trifluorophthalic acid. Decarboxylation results in a solution of 2,4,5-TiFBA in an organic decarboxylating solvent such as N-methylpyrrolidone (NMP).

Workup

  1. customIt is prepared by a process

Sources & evidence

ORD record
ord-a686d755eb7e48f7907bbac93e125a1f
Source dataset
uspto-grants-1994_08
Patent number
US05336806

Reaction notes

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