Dimethylformamide → 1,3(2H,4H)-isoquinolinedione

HRID 1814449Notes

Reaction equation

HRID 1814449 reaction equation
ClC1[N:3]=[C:4](N2CCN(CC)CC2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](=[O:23])([O-])[O-].[Cs+].[Cs+].CN(C)C=[O:29]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]1(=[O:23])[NH:3][C:4](=[O:29])[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=[C:10]2[CH2:11]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 22503669HCID 22503669, compound

Product 1

HCID 3494351,3(2H,4H)-isoquinolinedione

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3-Chloro-1-(4-ethylpiperazin-1-yl)isoquinoline (3.5 g) and 4-(1,3,2-dioxaborynan-2-yl)-1-(1,3-dioxolan-2-yl)benzene (5.0 g) were reacted in dimethylformamide (50 ml), in the presence of cesium carbonate (7.3 g) and tetrakistriphenylphosphinepalladium (0.3 g) at 80° C. in a nitrogen stream for 12 hr. The reaction solution was evaporated, and then partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 4.66 g of the title compound as a pale yellow oil. (17-5) 1-(4-Ethylpiperazin-1-yl)-3-(4-formylphenyl)isoquinoline

Workup

  1. customThe reaction solution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe resulting organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-03a85851618649aa8d5f7d5a82629d19
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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