Acetic Acid → 4-(3,5-Dichloro-pyridin-4-ylmethyl)-7-difluoromethoxy-2H-phthalazin-1-one

HRID 2268899Notes

Reaction equation

HRID 2268899 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH:8]=[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([F:21])[F:20])=[CH:15][CH:16]=2)[C:11](=O)[O:10]1.C(O)(=O)C.O.[NH2:29][NH2:30]>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([F:21])[F:20])=[CH:15][CH:16]=2)[C:11](=[O:10])[NH:30][N:29]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 53863513HCID 53863513, compound

Product 1

HCID 183816054-(3,5-Dichloro-pyridin-4-ylmethyl)-7-difluoromethoxy-2H-phthalazin-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,5-dichloro-pyridin-4-ylmethylen)-6-difluoromethoxy-3H-isobenzofuran-1-one (14.4 g, 21 mmoles), prepared as described in example 97, in CH3OH (100 ml), under N2, was added with acetic acid (3.6 ml, 63 mmoles) and hydrazine monohydrate (3.15 ml, 63 mmoles). A precipitate formed and the mixture was refluxed for 2 hours. After 1 night to stand the mixture was cooled over ice and the solid filtered and washed with little CH3OH. After drying under vacuum at 50° C., 6.64 g of the title compound were obtained [yield: 85% from (5-difluoromethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide].

Workup

  1. customA precipitate formed
  2. temperaturethe mixture was refluxed for 2 hours
  3. waitAfter 1 night to stand
  4. temperaturethe mixture was cooled over ice
  5. filtrationthe solid filtered
  6. washwashed with little CH3OH
  7. customAfter drying under vacuum at 50° C.

Sources & evidence

ORD record
ord-71eb324517cf4336a08283307e4a7155
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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