HCID 13309026, compound → HCID 13309028, compound

HRID 615144Notes

Reaction equation

HRID 615144 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:20])=[C:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:12]=2)[C:7](=[O:21])[C:6]([C:22]([O:24]CC)=[O:23])=[CH:5]1>[OH-].[Na+]>[F:20][C:10]1[CH:9]=[C:8]2[C:13](=[N:12][C:11]=1[C:14]1[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=1)[N:4]([CH:3]=[CH2:2])[CH:5]=[C:6]([C:22]([OH:24])=[O:23])[C:7]2=[O:21]

Participants

3

Reactant 1

HCID 13309026HCID 13309026, compound

Product 1

HCID 13309028HCID 13309028, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 1-(2-chloroethyl)-6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8-naphthyridine-3-carboxylate was suspended in 1N sodium hydroxide and the suspension was heated at 70° C. for 4 hours. The precipitate was collected by filtration, and dissolved in water. Then the pH of the solution was adjusted to about 6 with acetic acid. The resulting solid was collected and recrystallized from ethanol to give 6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1-vinyl-1,8-naphthyridine-3-carboxylic acid (Compound 2) (0.22 g, m.p. 254°-257° C.).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in water
  3. customThe resulting solid was collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4aeda7d70d574be88048f26d36b8938b
Source dataset
uspto-grants-1985_02
Patent number
US04497816

Reaction notes

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