Sodium Hydroxide → HCID 178462625, compound

HRID 851090Notes

Reaction equation

HRID 851090 reaction equation
C(OC(N1CCN([C:12]2[N:21]=[C:20]3[C:15]([C:16](=[O:27])[C:17]([C:24]([OH:26])=[O:25])=[CH:18][N:19]3[CH:22]=[CH2:23])=[CH:14][C:13]=2[F:28])CC1)=O)C.[OH-:29].[Na+]>>[F:28][C:13]1[CH:14]=[C:15]2[C:20](=[N:21][C:12]=1[OH:29])[N:19]([CH:22]=[CH2:23])[CH:18]=[C:17]([C:24]([OH:26])=[O:25])[C:16]2=[O:27]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 13054059HCID 13054059, compound

Product 1

HCID 178462625HCID 178462625, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(4-ethoxycarbonyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylic acid (78 g) and aqueous 20% sodium hydroxide (1,100 ml) was refluxed with stirring for 24 hours. After cooling, the resulting crystals were collected by filtration and washed with aqueous 10% sodium hydroxide (50 ml). The crystals were added to water (600 ml) and the mixture was heated at 90° C. and the acetic acid (50 ml) was added. After treatment with charcoal, the solution was acidified with concentrated hydrochloric acid (100 ml), and cooled in an ice-bath. The resulting crystals were collected by filtration, washed with water, and recrystallized from ethanol-chloroform to give 42.5 g of 6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylic acid, m.p. 256°-259° C.

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with aqueous 10% sodium hydroxide (50 ml)
  5. additionThe crystals were added to water (600 ml)
  6. additionthe acetic acid (50 ml) was added
  7. temperaturecooled in an ice-bath
  8. filtrationThe resulting crystals were collected by filtration
  9. washwashed with water
  10. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-6c1a136269244cdf8fa812699169c2a6
Source dataset
uspto-grants-1983_05
Patent number
US04382937

Reaction notes

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