Methyl iodide → 7-Methoxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one

HRID 1765347Notes

Reaction equation

HRID 1765347 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[K+].[K+].CI>O1CCCC1>[CH3:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:14])[CH3:15])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1363729927-Hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 211065847-Methoxy-2-Isopropyl-4-bromo-2H-phthalazin-1-oneYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7-Hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.4 g, 1.4 mmol) in tetrahydrofuran (THF) (5 ml) were added successively, K2CO3 (0.59 g, 4.3 mmol) and methyl iodide (0.22 g, 1.55 mmol) and the mixture was heated to reflux for 24 hours. After this time, LC-MS indicated complete consumption of starting material, and the reaction mixture was concentrated under vacuum. The residue was re-dissolved in ethyl acetate (50 ml) and washed with water (2×30 ml), the organic layer was dried (MgSO4), filtered and concentrated under vacuum to give the title compound (0.32 g, 76% yield) as an orange powder.

Workup

  1. temperatureto reflux for 24 hours
  2. customconsumption of starting material
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. dissolutionThe residue was re-dissolved in ethyl acetate (50 ml)
  5. washwashed with water (2×30 ml)
  6. dry with materialthe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-64a5920ef22a4b528d45d90ae7d125da
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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