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

HRID 1384134Notes

Reaction equation

HRID 1384134 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 1N aqueous sodium hydrogen carbonate 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 0C; 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-a60099173aa244a4969b2f1fb5f320f2
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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