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

HRID 1814448Notes

Reaction equation

HRID 1814448 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=C(Cl)[N:3]=1.C(N1CCNCC1)C.[C:21](=[O:24])([O-])[O-].[K+].[K+].CN(C)C=[O:30]>>[C:21]1(=[O:24])[NH:3][C:2](=[O:30])[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:6]2[CH2:5]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 2986251,3-Dichloroisoquinoline

Product 1

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

Procedure

1,3-Dichloroisoquinoline (9.30 g), N-ethylpiperazine (5.90 g) and potassium carbonate (10.0 g) were reacted in dimethylformamide (70 ml) at 70° C. for 5 hr. The reaction solution was evaporated and partitioned between ethyl acetate and water. The resulting organic phase was washed with water, dried and evaporated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 12.80 g of the title compound as a pale brown oil. (17-4) 3-[(1,3-Dioxolan-2-yl)phenyl]-1-(4-ethylpiperazin-1-yl)isoquinoline

Workup

  1. customThe reaction solution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe resulting organic phase 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-55b0160a211c4843bb9d191f7b70180d
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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