Phthalimide potassium salt → HCID 69315268, compound

HRID 2250480Notes

Reaction equation

HRID 2250480 reaction equation
Cl[CH:2]([CH3:15])[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C>[C:16]1(=[O:26])[N:20]([CH:2]([CH3:15])[CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[O:6])[C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 69315627HCID 69315627, compound

Product 1

HCID 69315268HCID 69315268, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-4′-methoxyvalerophenone (Rieke Metals) (2.26 g, 10.0 mmol) in DMF (10 mL) was added potassium phthalimide (1.85 g, 10 mmol mmol). The solution was heated under N2 (g) at 70° C. overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (70 mL) and water (50 mL). The organic layer was washed with another portion of water (50 mL), followed by saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL). The organic layer was dried (sodium sulfate) and concentrated to give a tan solid (2.73 g, 81% yield). MS m/e 220; HPLC retention time 3.52 min (Method A).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate (70 mL) and water (50 mL)
  3. washThe organic layer was washed with another portion of water (50 mL)
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8bee7747da98406ab6f2c303a800f08f
Source dataset
uspto-grants-2008_01
Patent number
US07317032B2

Reaction notes

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