Phosphorus oxychloride → 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2372074Notes

Reaction equation

HRID 2372074 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](O)[N:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:11]1[N:12]=[C:13]2[C:8]([C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[CH:9][C:10]=1[F:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178524694HCID 178524694, compound

Product 1

HCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Procedure

A suspension of 0.19 g (0.72 mmole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylic acid in 2 ml of phosphorus oxychloride was heated at reflux for one-half hour. The resulting solution was cooled to room temperature and the solvent was removed in vacuo. The residue was triturated with ice water and the resulting solid was removed by filtration, washed with water, then ether, and dried in vacuo to give 0.11 g of the title compound, mp 209-212° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one-half hour
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with ice water
  5. customthe resulting solid was removed by filtration
  6. washwashed with water
  7. dry with materialether, and dried in vacuo

Sources & evidence

ORD record
ord-d5c5a89f041442208e0415cfbddb463d
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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