2-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dimethoxy-benzonitrile

HRID 1186032Notes

Reaction equation

HRID 1186032 reaction equation
Br[C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[Cu][C:25]#[N:26]>CN1CCCC1=O>[O:15]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[N:5]1[CH2:4][C:3]1[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:2]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 88657072-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dioneHCID 178418546HCID 178418546, compound

Product 1

HCID 671887662-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dimethoxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-(2-bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione (26.63 g, 0.07079 mol) and copper (I) cyanide (12.7 g, 0.1416 mol) in N-methyl-2-pyrrolidinone (266 mL) was heated to reflux for 18 h under nitrogen. The resulting mixture was concentrated in vacuo and the resulting residue stirred with a mixture of chloroform (250 mL) and water (250 mL) for 30 min. The resulting suspension was filtered through CELITE and the layers separated. The organic layer was extracted with brine (2×), dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was crystallized from methylene chloride/methanol (500 mL) to yield 2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dimethoxy-benzonitrile as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h under nitrogen
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. filtrationThe resulting suspension was filtered through CELITE
  5. customthe layers separated
  6. extractionThe organic layer was extracted with brine (2×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting solid was crystallized from methylene chloride/methanol (500 mL)

Sources & evidence

ORD record
ord-19646c43804c4ab4a6bfab40820a7fc6
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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