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

HRID 620876Notes

Reaction equation

HRID 620876 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-e31297cecb90445ca5eb41528a596808
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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