m-Chloroperbenzoic acid → 5-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazin-3-oxide

HRID 1357006Notes

Reaction equation

HRID 1357006 reaction equation
[CH:1]1([O:6][C:7]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[N:10][N:11]=[C:12]3[CH2:19][C:20]2[C:25]([Cl:26])=[CH:24][N:23]=[CH:22][C:21]=2[Cl:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl>[CH:1]1([O:6][C:7]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[N+:10]([O-:36])[N:11]=[C:12]3[CH2:19][C:20]2[C:21]([Cl:27])=[CH:22][N:23]=[CH:24][C:25]=2[Cl:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 98659165-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine

Product 1

HCID 185048265-Cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazin-3-oxideYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution under stirring of 5-cyclopentyloxy-1-(3,5-dichloropyridin-4-ylmethyl)-6-methoxy-phthalazine (0.1 g, 0.741 mmoles), obtained as described in example 8, in methylene chloride (2 ml), was added with 55% m-chloroperbenzoic acid (255.75 mg, 0.816 mmoles). The mixture was diluted with methylene chloride, washed with a solution of NaHCO3, anhydrified and dried. The residue was flash chromatographed over silica gel (eluent:methylene chloride/ethyl acetate 1:1) and the eluate taken up in ether to give 0.2 g of the title product (yield: 64%).

Workup

  1. customobtained
  2. washwashed with a solution of NaHCO3
  3. customdried
  4. customchromatographed over silica gel (eluent:methylene chloride/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-7d7037ed2fb54a0297acf0dbaf613fc0
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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