Hydrochloric Acid → HCID 22386479, compound

HRID 2054191Notes

Reaction equation

HRID 2054191 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[NH:12][N:11]=2)[CH:2]=1.P(Cl)(Cl)([Cl:23])=O.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O1CCOCC1.O>[Cl:23][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:11][N:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 23440678HCID 23440678, compound

Product 1

HCID 22386479HCID 22386479, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

Under exclusion of air, 771 mg (2.9 mmol) 4-[3-(pyridin-3-yl)propyl]phthalazin-1(2H)-one in 14 ml acetonitrile is mixed with 1.11 g (7.25 mmol) phosphoryl chloride and 1.45 ml 4 N HCl in dioxane and stirred for 36 h at 45° C. Then 50 ml water is added, the reaction mixture adjusted to alkaline pH with sat. Na2CO3 solution and immediately extracted 3 times with EtOAc. Drying (Na2SO4) of the organic phases and evaporation yield the title compound; FAB-MS (M+H)+=284.

Workup

  1. extractionimmediately extracted 3 times with EtOAc
  2. customDrying
  3. custom(Na2SO4) of the organic phases and evaporation

Sources & evidence

ORD record
ord-70004534858b41799b23162299605117
Source dataset
uspto-grants-2008_02
Patent number
US07329660B2

Reaction notes

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