Water → HCID 21219072, compound

HRID 1585652Notes

Reaction equation

HRID 1585652 reaction equation
O=[C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[NH:3]1.O.[OH-].[NH4+].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:2]1[N:3]=[C:4]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychloride2×HCID 21219076HCID 21219076, compound

Product 1

HCID 21219072HCID 21219072, compound

Procedure

Heat a mixture of 8-oxo-6-(3-methyl-2-pyridinyl)-1,7-naphthyridine (16.4 g, 69.1 mmol) in phosphorus oxychloride (200 mL) on a steam bath for 3 hours. Remove excess phosphorus oxychloride under reduced pressure, cool in an ice-water bath and add ice (100 g) and water (100 mL). Add concentrated ammonium hydroxide to neutralize the solution, while maintaining the temperature below 10° C. Filter the resultant mixture, air dry the solids and triturate with boiling benzene (1 L). Concentrate the mixture, filter and crystallize the isolated solid from benzene to obtain the title compound, mp 130-1° C.

Workup

  1. temperatureHeat
  2. temperaturewhile maintaining the temperature below 10° C
  3. filtrationFilter the resultant mixture, air
  4. customdry the solids
  5. customtriturate with boiling benzene (1 L)
  6. concentrationConcentrate the mixture
  7. filtrationfilter
  8. customcrystallize the isolated solid from benzene

Sources & evidence

ORD record
ord-33caeaf873d744c38b910fe5535f0c03
Source dataset
uspto-grants-1999_08
Patent number
US05939431

Reaction notes

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