1-Chloro-4-(4-pyridinylmethyl)phthalazine → HCID 22741993, compound

HRID 1057724Notes

Reaction equation

HRID 1057724 reaction equation
[CH2:1](ONC1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]CC.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[N:22][N:21]=1.Cl.O1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C(O)C>[CH2:40]([O:41][C:42]1[CH:43]=[C:20]([CH:29]=[CH:28][CH:27]=1)[NH:21][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[N:22][N:21]=1)[CH2:39][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazineHCID 204431481,4-Dioxane hydrochlorideHCID 54200978HCID 54200978, compound

Product 1

HCID 22741993HCID 22741993, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 262 mg (1.05 mmol) decyloxyaniline (Salor) in 5 ml ethanol, 0.26 ml HCl/dioxane 4N is added, the mixture stirred for ≈3 min, and then 256 mg (1.00 mmol) 1-chloro-4-(4-pyridyl-methyl)phthalazine (Example 67A.1) is added. After 2 h boiling under reflux, the mixture is cooled and concentrated by evaporation. The residue is stirred with 6 ml NH3 solution (10% in water: or 10 ml sat. NaHCO3 solution) and 15 ml dichloromethane/methanol 50:1 for 30 min. The aqueous phase is then separated off and extracted again with dichloromethane. The organic phase is dried (Na2SO4) and concentrated by evaporation. Crystallization [possibly after chromatography on SiO2 (ethyl acetate/CH3OH, 19:1)] from acetonitrile (or methanol) yields the title compound: m.p.: 116-119° C.; Anal. calc.(C30H36N4O) C, 76.89%; H, 7.74%; N, 11.96%; found C, 76.7%; H, 7.7%; N, 11.9%; FAB MS (M+H)+=469.

Workup

  1. waitAfter 2 h boiling
  2. temperatureunder reflux
  3. temperaturethe mixture is cooled
  4. concentrationconcentrated by evaporation
  5. stirringThe residue is stirred with 6 ml NH3 solution (10% in water: or 10 ml sat. NaHCO3 solution) and 15 ml dichloromethane/methanol 50:1 for 30 min
  6. customThe aqueous phase is then separated off
  7. extractionextracted again with dichloromethane
  8. dry with materialThe organic phase is dried (Na2SO4)
  9. concentrationconcentrated by evaporation
  10. customCrystallization [possibly after chromatography on SiO2 (ethyl acetate/CH3OH, 19:1)] from acetonitrile (or methanol)

Sources & evidence

ORD record
ord-b19d42927bc040049c3b7afb7283ea93
Source dataset
uspto-grants-2003_02
Patent number
US06514974B2

Reaction notes

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