2-(2-(2,5-Dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dione → 2-(3-(2,5-Dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione

HRID 474342Notes

Reaction equation

HRID 474342 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:22])[CH2:10][N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21]>COC(OC)N(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[O:22])[C:10]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])=[CH:10][N:11]([CH3:19])[CH3:12]

Participants

3

Reactant 1

HCID 580633722-(2-(2,5-Dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dione

Product 1

HCID 666776892-(3-(2,5-Dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dioneYield 1,541.5%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 2-(2-(2,5-dichlorophenyl)-2-oxoethyl)isoindoline-1,3-dione (0.10 g, 0.30 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (8 mL) was heated at reflux for 2 hours. The resultant mixture was then concentrated. Purification by flash column chromatography afforded 2-(3-(2,5-dichlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione as a solid (0.90 g, 77% yield).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe resultant mixture was then concentrated
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-75ab1d99461f4a50bd93d512879c4cab
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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