Nitrogen → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine 3-oxide

HRID 2268830Notes

Reaction equation

HRID 2268830 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[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)[CH:12]=[N:11][N:10]=1.N#N.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[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)[CH:12]=[N+:11]([O-:32])[N:10]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 70297m-Chloroperbenzoic acidHCID 9927063HCID 9927063, compound

Product 1

HCID 183816651-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine 3-oxideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1 g, 3.13 mmoles), prepared as described in example 5, in dry CH2Cl2 (15 ml), under stirring and N2 at room temperature, was added with m-chloroperbenzoic acid (0.81 g, 4.7 mmoles). After 1 hour the mixture was washed with 10% NaOH and water, anhydrified and brought to dryness. The residue was flash chromatographed (eluent: ethyl acetate 100%, then ethyl acetate/CH3OH 8:2) to give a solid which was crystallised from acetic acid/ethyl acetate to give 0.32 g of the title compound (yield: 31%). m.p.>230° C.

Workup

  1. washAfter 1 hour the mixture was washed with 10% NaOH and water
  2. customchromatographed (eluent
  3. customethyl acetate 100%, then ethyl acetate/CH3OH 8:2) to give a solid which
  4. customwas crystallised from acetic acid/ethyl acetate

Sources & evidence

ORD record
ord-7fde72c0f0cf427cb7dbe40e8cdd80ca
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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