Nitric Acid → HCID 178524694, compound

HRID 622569Notes

Reaction equation

HRID 622569 reaction equation
[N+]([O-])(O)=[O:2].[CH:5]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:24])=[C:15](N4CCNCC4)[N:16]=3)[C:11](=[O:25])[C:10]([C:26]([OH:28])=[O:27])=[CH:9]2)[CH2:7][CH2:6]1>S(=O)(=O)(O)O>[CH:5]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:24])=[C:15]([OH:2])[N:16]=3)[C:11](=[O:25])[C:10]([C:26]([OH:28])=[O:27])=[CH:9]2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4654511,8-Naphthyridine-3-carboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 178524694HCID 178524694, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2 ml of 70% nitric acid in 10 ml of 98% sulfuric acid was added in portions 1.0g (3.0 mmole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid, keeping the temperature between 25°-30° C. The resulting solution was stirred at room temperature for 18 hours and poured onto 40 g of ice. The mixture was stirred at room temperature for 24 hours, concentrated in vacuo, the pH adjusted to 12 with aqueous sodium hydroxide, and filtered through a fiber glass pad. The filtrate was acidified to pH 3.5 with 6.0M hydrochloric acid, the resulting precipitate removed by filtration, washed with water then ether and dried in vacuo to give 0.23 g of the title compound, mp 325°-327° C.

Workup

  1. custombetween 25°-30° C
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered through a fiber glass pad
  5. customthe resulting precipitate removed by filtration
  6. washwashed with water
  7. dry with materialether and dried in vacuo

Sources & evidence

ORD record
ord-a252a9dd62d142e59bd627ec5fd17e98
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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