Phosphorus oxychloride → 7-Acetamino-1-chloro-4-(4-pyridylmethyl)phthalazine

HRID 49873Notes

Reaction equation

HRID 49873 reaction equation
Cl.[NH:2]([C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[N:11][N:12]=[C:13]2O)=[CH:8][CH:7]=1)[C:3]([CH3:5])=[O:4].O=P(Cl)(Cl)[Cl:26].C([O-])(O)=O.[Na+]>C(#N)C.O>[NH:2]([C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[N:11][N:12]=[C:13]2[Cl:26])=[CH:8][CH:7]=1)[C:3]([CH3:5])=[O:4]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178474031HCID 178474031, compound

Product 1

HCID 227419517-Acetamino-1-chloro-4-(4-pyridylmethyl)phthalazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

Under a nitrogen atmosphere, a suspension of 2.24 g (7.6 mmol) 7-acetamino-1-hydroxy-4-(4-pyridylmethyl)phthalazine hydrochloride (=1-oxo-4-[pyridyl-(4′)-methyl]-7-acetamino-1,2-dihydrophthalazine hydrochloride: for preparation see German Auslegeschrift no. 1 061 788 [published Jul. 23, 1959]) in 22 ml acetonitrile is spiked with 1.74 ml (19 mmol) phosphoroxychloride and heated for 4 h to 95° C. The mixture is cooled to 10° C., and 7.5 g NaHCO3 in 30 ml water is added. The deep-red suspension is stirred for 15 min, filtered, and washed out with water. Drying under HV yields the title compound: HPLC: tRet(Grad5-40)=10.2; FAB MS (M+H)+=313.

Workup

  1. temperatureheated for 4 h to 95° C
  2. filtrationfiltered
  3. washwashed out with water
  4. customDrying under HV

Sources & evidence

ORD record
ord-82bde1016e44479089ea8980f61ac773
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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