Phosphorus oxychloride → 1-Chloro-4-(4-pyridinylmethyl)phthalazine

HRID 1384147Notes

Reaction equation

HRID 1384147 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=O)[NH:10][N:9]=2)=[CH:3][CH:2]=1.Cl.O1CCOCC1.P(Cl)(Cl)([Cl:28])=O.C([O-])(O)=O.[Na+]>C(#N)C.O>[Cl:28][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[N:9][N:10]=1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinoneHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Under exclusion of air, 29 g (122 mmol) 4-(4-pyridylmethyl)-1 (2H)-phthalazinone [for preparation, see German Auslegeschrift no. 1061788 (published 23.7.1959)] in 450 ml acetonitrile is mixed with 61 ml HCl/dioxane 4N and 28 ml (306 mmol) phosphoryl chloride and stirred for 27 h at 50° C. To the white suspension, 119 g NaHCO3 in 1.45 l water is then added dropwise under ice cooling, and the mixture is stirred and the title compound filtered off. Anal. calc. (C14H10N3Cl) C 65.76%, H 3.94%, N 16.43%, Cl 13.86%; found C 65.40%, H 4.12%, N 16.45%, Cl 13.66%; FAB MS (M+H)+=256.

Workup

  1. stirringthe mixture is stirred
  2. filtrationthe title compound filtered off

Sources & evidence

ORD record
ord-132d44200e8944a6adea7a5f4dcec0b6
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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