Ethyl 5-bromovalerate → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-pentanoic acid ethyl ester

HRID 346243Notes

Reaction equation

HRID 346243 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C)C=O>[CH2:9]([O:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:15]1[C:11](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]1=[O:16])[CH3:10]

Participants

4

Reactant 2

HCID 84580Ethyl 5-bromovalerateHCID 24194345Phthalimide potassium salt

Product 1

HCID 541172071,3-Dihydro-1,3-dioxo-2H-isoindole-2-pentanoic acid ethyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure used to prepare 1,3-dihydro-1,3-dioxo-2H-isoindole octanoic acid ethyl ester. Thus, a mixture of 100 g (0.48 mole) of ethyl 5-bromovalerate (99%, Aldrich) and 94.5 g (0.50 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide gave 107.6 g (81%) of viscous oil. A 2.0 g sample of this oil was purified by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:10). Fractions containing title compound were combined and the solvents evaporated under reduced pressure to give 1.9 g (95% recovery) of colorless liquid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-dca49eb278f44e80b0477e8e836ddd19
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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