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

HRID 2268855Notes

Reaction equation

HRID 2268855 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-de5bc3bb59bf45efa7f95d7cfc09dd6f
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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