Potassium Carbonate → HCID 86683219, compound

HRID 1852147Notes

Reaction equation

HRID 1852147 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[NH:10][N:9]=1.Br[CH2:20][CH2:21][O:22][CH3:23]>O>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]([CH2:20][CH2:21][O:22][CH3:23])[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 27751424-chlorophthalazin-1(2H)-one

Product 1

HCID 86683219HCID 86683219, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (459 mg, 3.32 mmol) was added to a solution of 4-chlorophthalazin-1(2H)-one (300 mg, 1.661 mmol) and 1-bromo-2-methoxyethane (462 mg, 3.32 mmol) and heated to 50° C. for 3 hrs. After 3 hrs the reaction was diluted with water and extracted with EtOAc (2×). The organic layer was washed with water followed by brine, dried over MgSO4, filtered and evaporated to give the crude product. The crude material was purified via silica gel chromatography (90 g column, 5-45% EtOAc:Hex) to give the desired product 4-chloro-2-(2-methoxyethyl)phthalazin-1(2H)-one (280 mg, 70.6% yield) as a yellow solid. MS: MS m/z 223.15(M++1).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product
  7. customThe crude material was purified via silica gel chromatography (90 g column, 5-45% EtOAc:Hex)

Sources & evidence

ORD record
ord-fdbd1b61cb5b480ca055f13eab138836
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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