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

HRID 2297426Notes

Reaction equation

HRID 2297426 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[C:11](=O)[O:10]1.O.[NH2:23][NH2:24]>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[C:11](=[O:10])[NH:24][N:23]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 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

A suspension of 3-(3,5-dichloro-pyridin-4-ylmethylene)-6-methoxy-3H-isobenzofuran-1-one (84.4 g, 0.126 mole), prepared as described in example 37, in CH3OH (200 ml) under N2 was added with hydrazine monohydrate (18.4 ml, 0.378 mole). The mixture was refluxed for 1 hour, then left overnight at room temperature and cooled over ice. The solid was filtered, washed with cold CH3OH and dried in oven at 50° C. under vacuum; 33.3 g of the title compound were thus obtained (yield: 80%). m.p.: 259-262° C.

Workup

  1. customprepared
  2. temperatureThe mixture was refluxed for 1 hour
  3. temperaturecooled over ice
  4. filtrationThe solid was filtered
  5. washwashed with cold CH3OH
  6. customdried in oven at 50° C. under vacuum

Sources & evidence

ORD record
ord-36ae9338e1aa4409810a751408623e45
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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