HCID 178500753, compound → Methyl 8-fluoro-4-hydroxy-7-methylquinoline-2-carboxylate

HRID 922795Notes

Reaction equation

HRID 922795 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[N:9]=[C:10](\[CH2:15][C:16]([O:18]C)=O)/[C:11]([O:13][CH3:14])=[O:12]>CC(N(C)C)=O>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][C:16]2=[O:18]

Participants

3

Reactant 1

HCID 178500753HCID 178500753, compound

Product 1

HCID 89543481Methyl 8-fluoro-4-hydroxy-7-methylquinoline-2-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Dimethyl(2E)-2-[2-fluoro-3-methylphenyl)imino]butanedioate (7-6, 3.27 g, 12.24 mmol) in DMA (24.47 ml) was heated at 240° C. in the microwave for 5 min. The solvent was evaporated under reduced pressure and the residue triturated with ether to afford a tan solid. The desired product was filtered off and washed with ether till the ether ran colorless affording Methyl 8-fluoro-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (7-7, 1.23 g, 43% yield) as a tan solid, LCMS shows 93% pure, LRMS m/z (M+H)+ 236.1 found, 236.1 required.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue triturated with ether
  3. customto afford a tan solid
  4. filtrationThe desired product was filtered off
  5. washwashed with ether till the ether

Sources & evidence

ORD record
ord-112110b5522e43ba8a0beb6ba18933e4
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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