Ethyl 4-(3-chloropropoxy)benzoate → ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoate

HRID 346231Notes

Reaction equation

HRID 346231 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14]Cl)=[CH:7][CH:6]=1)[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 52199766ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]benzoateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a stirred solution of 22.5 g (0.092 mole) of 4-(3-chloropropoxy)benzoic acid ethyl ester in 150 mL of dimethylformamide was added 17.6 g (0.093 mole) of potassium phthalimide (98%, Aldrich) and the mixture was heated (135° C.) under a nitrogen atmosphere for 8 hr. The solvent was evaporated under reduced pressure to leave a semi-solid residue. The residue was triturated with 100 mL of water and the resulting solid was collected by filtration. The solid was recrystallized from isopropyl alcohol to yield 18.2 g (55%) of title compound as an off-white solid, mp 106°-108° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto leave a semi-solid residue
  3. customThe residue was triturated with 100 mL of water
  4. filtrationthe resulting solid was collected by filtration
  5. customThe solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5b2a426afd5b47d6ac3fd459e8cc4820
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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