HCID 13309023, compound → HCID 13309024, compound

HRID 615142Notes

Reaction equation

HRID 615142 reaction equation
[F:1][C:2]1[C:3]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[N:4][C:5]([NH:8][CH:9]=[C:10]([C:16](OCC)=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[N:4][C:3]=1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[NH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]2=[O:17]

Participants

3

Reactant 1

HCID 13309023HCID 13309023, compound

Product 1

HCID 13309024HCID 13309024, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A suspension of diethyl N-[3-fluoro-2-(4-pyridyl)-6-pyridyl]aminomethylenemalonate (11.5 g) in 120 ml of Dowtherm A was heated to reflux for 10 minutes and then cooled to room temperature. The resulting solid was filtered off. The filtrate was heated to reflux for 10 minutes and the solid was collected. The combined solid was washed successively with ethanol and ether to give ethyl 6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylate (7.2 g, m.p. 280°-285° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 minutes
  3. filtrationThe resulting solid was filtered off
  4. temperatureThe filtrate was heated
  5. temperatureto reflux for 10 minutes
  6. customthe solid was collected
  7. washThe combined solid was washed successively with ethanol and ether

Sources & evidence

ORD record
ord-77bb46aaea174c339418146c6324237a
Source dataset
uspto-grants-1985_02
Patent number
US04497816

Reaction notes

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