Water → HCID 67072761, compound

HRID 386543Notes

Reaction equation

HRID 386543 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][NH:5][C:4](=[O:14])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.O>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:4](=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 27358035-Chloro-6-phenylpyridazin-3(2H)-one

Product 1

HCID 67072761HCID 67072761, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-chloro-6-phenylpyridazin-3(2H)-one (207 mg, 1.0 mmol) in DMF (3 mL) at room temperature under argon was added K2CO3 (415 mg, 3.0 mmol), and followed by addition of 1-(bromomethyl)-4-methoxybenzene (241 mg, 1.2 mmol). The resulting reaction mixture was stirred at room temperature overnight. Water (25 mL) was added to the reaction mixture and stirred for 1 hour. The product was collected by filtration and dried overnight under reduce pressure to yield 278 mg (81%) of 5-chloro-2-(4-methoxybenzyl)-6-phenylpyridazin-3(2H)-one as a tan solid. MS (ESI) 327 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 1 hour
  3. filtrationThe product was collected by filtration
  4. customdried overnight

Sources & evidence

ORD record
ord-62a839ca096e435c8569966c00b0a154
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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