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

HRID 2297470Notes

Reaction equation

HRID 2297470 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 538635133-(3,5-Dichloro-pyridin-4-ylmethylene)-6-difluoromethoxy-3H-isobenzofuran-1-one

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-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-f6e8483fc4014c33b93515248ebf0690
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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