Potassium Carbonate → 3-(4-methoxyphenyl)isoquinolin-1(2H)-one

HRID 1814444Notes

Reaction equation

HRID 1814444 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.C(N1CCNCC1)C.C(=O)([O-])[O-:29].[K+].[K+]>CN(C)C=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[NH:3][C:2](=[O:29])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 123280893-(4-methoxyphenyl)isoquinolin-1(2H)-oneYield 123%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-chloro-3-(4-methoxyphenyl)isoquinoline (0.89 g), N-ethylpiperazine (0.86 g) and potassium carbonate (1.10 g) was heated in dimethylformamide (20 ml) at 90° C. for 12 hr. The reaction mixture was evaporated, water was added to the resulting residue, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water and brine, dried over magnesium sulfate, and then the solvent was romoved. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound as a pale brown oil (1.02 g, yield; 88%).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the resulting residue
  3. extractionit was extracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-c2d9107d0c544ce5b7611ebbf1ebc58d
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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