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

HRID 868134Notes

Reaction equation

HRID 868134 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 1/2 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 1/2 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-799e0a28f5cf41fa9d19b89206cc7648
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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