m-Chloroperbenzoic acid → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine-3-oxide

HRID 49892Notes

Reaction equation

HRID 49892 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)([O-])O.[Na+]>C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[N+:9]([O-:34])[N:8]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 151194VatalanibHCID 516892Sodium Bicarbonate

Product 1

HCID 227419791-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine-3-oxide

Reagents, catalysts & solvents 1

HCID 175AcetateSolvent

Procedure

A mixture of 1.53 g (4.41 mmol) 1-(4-chloroanilino)-4-(4-pyridylmethyl)phthalazine (see Example 4), 1.74 g (about 5.75 mmol) 3-chloroperbenzoic acid (about 57%), and 80 ml acetate is stirred for 1 h at RT. Then 25 ml 1 N aqueous sodium hydrogencarbonate solution is added to the reaction mixture, which is stirred for 10 min, filtered, washed with water, then acetate, and the filter residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm, using an acetate/methanol mixture (19:1). Title compound is obtained after evaporation of the product-containing fractions under vacuum and recrystallization of the filter residue from methanol; m.p. 226-228° C.; ESI-MS: (M+H)+=363.

Workup

  1. stirringis stirred for 10 min
  2. filtrationfiltered
  3. washwashed with water
  4. customacetate, and the filter residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm

Sources & evidence

ORD record
ord-8d37997873f64d438ea2dff8884fd972
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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