Phosphorus oxychloride → HCID 22004370, compound

HRID 324342Notes

Reaction equation

HRID 324342 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH:7][N:6]=[C:5]2[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:8]1[C:9]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)[C:5]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:6][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22004359HCID 22004359, compound

Product 1

HCID 22004370HCID 22004370, compound

Procedure

6-Chloro-4-(3-pyridylmethyl)-1(2H)-phthalazinone (0.86 g) was suspended in 10 ml of phosphorus oxychloride. The obtained suspension was heated under reflux for 2 hours and freed from the phosphorus oxychloride by vacuum distillation. The residue was dissolved in tetrahydrofuran. The obtained solution was neutralized with triethylamine, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by vacuum distillation. The residue was purified by silica gel column chromatography to give 0.49 g of the title compound as a pale yellow crystal.

Workup

  1. temperatureThe obtained suspension was heated
  2. temperatureunder reflux for 2 hours
  3. distillationfreed from the phosphorus oxychloride by vacuum distillation
  4. dissolutionThe residue was dissolved in tetrahydrofuran
  5. additionfollowed by the addition of water
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  9. distillationfreed from the solvent by vacuum distillation
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-00d4186e303142b59f4d853a03d24712
Source dataset
uspto-grants-2001_04
Patent number
US06218392B1

Reaction notes

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