Hydrochloric Acid → HCID 22386465, compound

HRID 2054187Notes

Reaction equation

HRID 2054187 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[NH:11][N:10]=2)[CH:2]=1.P(Cl)(Cl)([Cl:22])=O.Cl>C(#N)C.O1CCOCC1>[Cl:22][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:10][N:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 22386474HCID 22386474, compound

Product 1

HCID 22386465HCID 22386465, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Under exclusion of air, 2.4 g (9.55 mmol) 4-[2-(pyridin-3-yl)ethyl]phthalazin-1(2H)-one in 36 ml acetonitrile is mixed with 2.18 ml (23.8 mmol) phosphoryl chloride and 4.75 ml 4 N HCl in dioxane and stirred for 3.5 h at 60° C. After cooling to RT, the product is filtered off as hydrochloride and washed with CH3CN. The crystals are dissolved in about 10 ml H2O, mixed with 15 ml H2O and 1.5 ml sat. NH3 solution and extracted immediately 3 times with EtOAc. Drying (Na2SO4) of the organic phases and evaporation yield the title compound; FAB-MS (M+H)+=270.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe product is filtered off as hydrochloride
  3. washwashed with CH3CN
  4. dissolutionThe crystals are dissolved in about 10 ml H2O
  5. additionmixed with 15 ml H2O and 1.5 ml sat. NH3 solution
  6. extractionextracted immediately 3 times with EtOAc
  7. customDrying
  8. custom(Na2SO4) of the organic phases and evaporation

Sources & evidence

ORD record
ord-602ee3aa39f24245af8cd4fa38b0a49e
Source dataset
uspto-grants-2008_02
Patent number
US07329660B2

Reaction notes

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