Nitric Acid → HCID 178524694, compound

HRID 620875Notes

Reaction equation

HRID 620875 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 1.0 g (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 6.0 M 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-86cdbd1612c5480aa547ee97e22dbd11
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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