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

HRID 2398248Notes

Reaction equation

HRID 2398248 reaction equation
O[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([OH:14])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:18])=O>O>[Cl:18][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7]([C:12]([OH:14])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178524789HCID 178524789, compound

Product 1

HCID 134959547-Chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-Dihydro-7-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylic acid (10 g) and phosphoryl chloride (20 ml) were stirred and heated at 100° for 2.5 hours. The mixture was cooled and poured into iced water (800 ml). The solid was filtered off and crystallized from dimethylformamide, m.p. 271°-273° (87%).

Workup

  1. temperatureheated at 100° for 2.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe solid was filtered off
  4. customcrystallized from dimethylformamide, m.p. 271°-273° (87%)

Sources & evidence

ORD record
ord-299fc37f3d494a799d82205ac5b159b9
Source dataset
uspto-grants-1977_05
Patent number
US04024255

Reaction notes

Loading…