4-Chloro-6-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile → 4-Chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901274Notes

Reaction equation

HRID 901274 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5](CC2C=CC(OC)=CC=2)[C:4](=[O:22])[C:3]=1[C:23]#[N:24]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([F:12])[CH:10]=2)[NH:5][C:4](=[O:22])[C:3]=1[C:23]#[N:24]

Participants

3

Reactant 1

HCID 692166344-Chloro-6-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 692171714-Chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-Chloro-6-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile (94) (4.3 g, 12.50 mmol) in neat TFA was refluxed for 24 h. The solution was cooled and excess TFA was distilled off under reduced pressure. The residue was taken in water, basified by solid NaHCO3 and filtered. The solids were washed with excess water and dried to yield 2.6 g (96%) of 4-chloro-6-fluoro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (96) as white solids. MP: 272° C.; 1H-NMR (DMSO-d6): δ 8.26 (dd, J=2.8, 8.2 Hz, 1H), 8.81 (d, J=2.8 Hz, 1H), 13.03 (S, 1H); EIMS: 224 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. distillationexcess TFA was distilled off under reduced pressure
  3. filtrationfiltered
  4. washThe solids were washed with excess water
  5. customdried

Sources & evidence

ORD record
ord-989d535956fc4ca3aef1b37665bf91e1
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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