Hydrogen Peroxide → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-4-[1,2,4]triazol-1-yl-phthalazine 3-oxide

HRID 2297465Notes

Reaction equation

HRID 2297465 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[N:11][N:10]=1.OO.[OH-].[Na+].C(OCC)(=[O:33])C.C(OCC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[N+:11]([O-:33])[N:10]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 98215811-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-4-[1,2,4]triazol-1-yl-phthalazineHCID 21584169Diethylether ethylacetate

Product 1

HCID 183816001-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-4-[1,2,4]triazol-1-yl-phthalazine 3-oxideYield 41%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under N2 at 0° C. a solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-4-[1,2,4]triazol-1-yl-phthalazine (5.1 g, 13.2 mmoles), prepared as described in example 51, in trifluoroacetic acid (25 ml), was dropwise added with H2O2 (1.35 ml, 13.5 mmoles). The temperature was left to rise to the room value and, after 48 hours, the pH was adjusted with NaOH. After further 24 hours under stirring, the mixture was dried, taken up in CH2Cl2. The organic phase was washed with water, anhydrified and dried to give a foam which was flash chromatographed (eluent: ethyl acetate/ethyl ether 6:4, then 8:2) to give 2.2 g of the title compound (yield: 41%). m.p.: 218-220° C. (dec.).

Workup

  1. waitThe temperature was left
  2. customthe mixture was dried
  3. washThe organic phase was washed with water
  4. customdried
  5. customto give a foam which
  6. customchromatographed (eluent

Sources & evidence

ORD record
ord-eef13a0a849b42958286bef62ea56b95
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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