Hydrazine → 4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one

HRID 1060583Notes

Reaction equation

HRID 1060583 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:23])[C:9]=1[CH:10]=[C:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13](=O)[O:12]1>CO>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:23])[C:9]=1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13](=[O:12])[NH:2][N:1]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 54395392HCID 54395392, compound

Product 1

HCID 224827114-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine (18.4 ml, 0.378 moles) was added to a suspension of 3-(3,5-dichloro-pyridin-4-ylmethylen)-6-methoxy-3H-isobenzofuran-1-one (24.4 g, 0.126 moles), obtained as described in example 11, in CH3OH (200 ml), under N2. The mixture was heated under reflux for 1 hour, then kept overnight at room temperature, cooled in ice, and the solid was filtered, washed with very cold CH3OH and dried in oven at 50° C. under vacuum, to give 33.3 g of the title compound (yield: 80%). m.p.: 259-262° C.

Workup

  1. customobtained
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. temperaturecooled in ice
  5. filtrationthe solid was filtered
  6. washwashed with very cold CH3OH
  7. customdried in oven at 50° C. under vacuum

Sources & evidence

ORD record
ord-b71d6898ba4f47e7b71d1514e23c55c0
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

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