Nitric Acid → HCID 15511752, compound

HRID 1358203Notes

Reaction equation

HRID 1358203 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH2:10]([O:12][P:13]([C:18]1[C:19](=[O:29])[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([Cl:28])[CH:22]=2)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11]>>[CH2:10]([O:12][P:13]([C:18]1[C:19](=[O:29])[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([N+:1]([O-:4])=[O:2])=[C:23]([Cl:28])[CH:22]=2)(=[O:17])[O:14][CH2:15][CH3:16])[CH3:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 15511751HCID 15511751, compound

Product 1

HCID 15511752HCID 15511752, compound

Procedure

55 ml of nitric acid are added dropwise to a solution of 55 ml of 96% sulphuric acid cooled in an ice bath, and then (7-chloro-2-oxo-1,2-dihydro-3-quinolyl)phosphonic acid diethyl ester (14.7 g, 46.6 mmol) is added in portions whilst maintaining the temperature at less than or equal to 5° C. When the addition is complete, stirring is continued for 15 minutes and then the ice bath is withdrawn and the reaction mixture is brought to ambient temperature over a period of about 1 hour 30 minutes. The solution is poured into ice and the precipitate is stirred to obtain a filterable solid. Filtration is carried out, followed by washing with water to neutrality and drying in vacuo. The solid is suspended in 210 ml of ethanol at reflux; the batch is left to cool and, after drying, filtered to obtain the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturewhilst maintaining the temperature at less than or equal to 5° C
  3. additionWhen the addition
  4. customthe ice bath is withdrawn
  5. waitthe reaction mixture is brought to ambient temperature over a period of about 1 hour 30 minutes
  6. additionThe solution is poured into ice
  7. stirringthe precipitate is stirred
  8. customto obtain a filterable solid
  9. filtrationFiltration
  10. washby washing with water to neutrality
  11. customdrying in vacuo
  12. temperatureat reflux
  13. waitthe batch is left
  14. temperatureto cool
  15. customafter drying
  16. filtrationfiltered

Sources & evidence

ORD record
ord-51a0eb9346914da68df08502f8f2f8d8
Source dataset
uspto-grants-2003_07
Patent number
US06596709B1

Reaction notes

Loading…