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

HRID 901275Notes

Reaction equation

HRID 901275 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([Cl: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]([Cl:12])[CH:10]=2)[NH:5][C:4](=[O:22])[C:3]=1[C:23]#[N:24]

Participants

3

Reactant 1

HCID 692163924,6-Dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

Product 1

HCID 692174464,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4,6-dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile (95) (8.2 g, 22.70 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 5.2 g (96%) of 4,6-dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (97) as yellow solids. MP: 247° C.; 1H-NMR (DMSO-d6): δ 8.45 (dd, J=2.4 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H), 13.17 (S, 1H); EIMS: 240 (M).

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-2db0ae8b238c4f8797d6b44e873a952d
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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