Acetic Acid → 1-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-yl]-ethanone

HRID 2268843Notes

Reaction equation

HRID 2268843 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.[C:24](O)(=[O:26])[CH3:25]>[Pd]>[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)[CH2:12][N:11]([C:24](=[O:26])[CH3:25])[N:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 947NitrogenHCID 9927063HCID 9927063, compound

Product 1

HCID 183816741-[4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-1H-phthalazin-2-yl]-ethanoneYield 50%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1 g, 3.12 mmoles), prepared as described in example 5, in glacial acetic acid (30 ml) under stirring and N2 was added with 10% Pd/C in catalytic amount, and the solution was put in a hydrogenator at 4 atmospheres. After 2 days the mixture was filtered and brought to dryness. The residue was flash chromatographed (eluent: hexane/ethyl acetate 3:7) to give 0.5 g of the title compound (yield: 50%). m.p.: 186-188° C.

Workup

  1. filtrationAfter 2 days the mixture was filtered
  2. customchromatographed (eluent: hexane/ethyl acetate 3:7)

Sources & evidence

ORD record
ord-ccf25600a7664690af1080d78bb45417
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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