HCID 59699605, compound → HCID 59699556, compound

HRID 901243Notes

Reaction equation

HRID 901243 reaction equation
COC1C=CC(C[N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11]([Cl:18])=[C:10]([C:19]#[N:20])[C:9]2=[O:21])=CC=1>C(O)(C(F)(F)F)=O>[Cl:18][C:11]1[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[NH:8][C:9](=[O:21])[C:10]=1[C:19]#[N:20]

Participants

3

Reactant 1

HCID 59699605HCID 59699605, compound

Product 1

HCID 59699556HCID 59699556, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(4-methoxybenzyl)-4-chloro-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carbonitrile (32) (326 mg, 1 mmol) in 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 197 mg (95%) of 4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (31) as white solids. MP: 310° C.; 1H-NMR (DMSO-d6): δ 7.58 (dd, J=4.4, 8.0 Hz, 1H), 8.50 (d, J=2.0, 8.0 Hz, 1H), 8.83 (dd, J=4.4, 1.6 Hz, 1H), 13.03 (s, 1H); EIMS: 206 (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-ed83c6c2770e4549810a41ec0720540e
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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